Six Of The Best Chess Game Players Biggest Upsets

best chess game upsets

Have you ever wanted to see some of the best chess players lose? Or want to know their biggest game upsets?

There are many reasons why chess is very popular in the world.

It’s because of the talented chess players great enthusiasm for the game; they are the masters of the chess game…

This chess Grandmasters have devoted their whole life to the game and gained colossal fame.

But most of the great chess players that we know from history did not even bother about becoming famous – they love the game, and they love analyzing the game and finding solutions for every move in chess.

These Chess Grandmasters are amazing to watch, but they are not invincible, of course.

They can be beaten in chess, and in this article, we are going to look at some of this Great Chess Grandmasters and let’s witness and learn from some of the games where they had some chess upsets.

Here are 6 of the Grandmasters some chess loses in their life.

Six Of The Best Chess Game Players Biggest Upsets In their Chess Life

Don’t forget to check out this article:
“Valuable Chess history you need to learn” click here to read blog post!

1. Paul Morphy

He is an American Chess Player, born on June 22, 1837, in New Orleans, Louisiana, United States.

Chess experts described Morphy as an excellent chess legend, having spectacular chess talent at a very young age. In 1857, he competed in the First American Chess Congress, with sixteen chess competitors and he ended up being first.

He received his M.A. at the age of eighteen, and at one point in his career tried to practice law but was not very successful at it.

In chess, it was his father that introduced him to the game at an early age, and he was a genius at the game defeating the best chess players in New Orleans at the age of twelve.

Paul Morphy had a great love for the game of chess that he wanted to compete against the best in the world, and one of them was the British chess champion, Staunton.

Morphy was not able to play with him because Staunton refused his challenge. The frustration of wanting to play and defeat the best chess player in the world became his downfall.

He is brilliant and indeed one of the best chess players in the world, but not exempted to losing a chess game of course.

Let’s look at Paul Morphy’s chess game upset.

Morphy Loses in Chess Game

Overlooked A Forced Mate

Morphy is considered to be an aggressive chess player and mostly build his attacks by sacrifices…

He has this tendency to get discouraged in a game where he is in an uncomfortable game and misses obvious threats from his opponents.

Like this game with Schulten, in 1857, Morphy played Black, and as expected he was playing aggressive moves early on the game.

Chess experts were saying that he could have made more sound moves than continuously playing aggressive moves.

See chess position below:

best chess game upset of Paul Morphy

After Morphy’s, Black Bishop captured the Knight, and White takes Bishop…

Instead of castling, some chess expert was saying that Morphy could have attacked the White King with its Black Queen.

See chess position below:

Also read: Advanced Chess Strategies That Will Help Improve Your Game

best chess game upset

Maybe surprised by Schulten being aggressive as well, he misjudged the situation and moved his Rook planning for a discovered check.

But…

Chess experts were suggesting that a better moved was Knight capturing Bishop first.

See chess position below:

best chess game

There was an obvious threat from White with its Queen on the h file, but Morphy was not bothered about it; instead, he moved his Bishop.

But a better move could have been protecting the h file from a threat of checkmate by moving its Knight instead.

See chess position below:

chess upset

Morphy was focused on his attacks on White’s Queenside, totally ignoring White’s real threat with its Queen.

After Morphy captured White’s Bishop, thinking he gain a material advantage, White has made its final move with its pawn.

An overlooked moved that caused Morphy’s defeat to Schulten. It was a beautiful forced mate, and there was nothing Paul Morphy could do if there is it is too late.

Morphy resigned, many chess experts were saying that this is not how Paul Morphy plays and nobody expected him to miss that move.

Check out the chess game and notation below:

chess upset for Morphy

1. e4 e5 2. f4 d5 3. exd5 e4 4. ♘c3 ♘f6 5. ♗c4 c6 6. d3 ♗b4 7. dxe4 ♘xe4 8. ♗d2 ♗xc3 9. ♗xc3 O-O 10. ♕h5 ♖e8 11. O-O-O ♘xc3 12. bxc3 ♕a5 13. ♔b2 g6 14. ♕h6 ♗g4 15. ♘f3 ♗xf3 16. gxf3 b5 17. f5 bxc4 18. f6

2. Wilhelm Steinitz

Steinitz is an American Chess Player, born in Prague on May 14, 1836…

During 1862, Wilhelm Steinitz was recognized as the best player in Austria, yes he was an Austrian and then later became an American Chess Player.

He competed in the London International Tournament where he finished second behind Anderssen.

Steinitz was playing like Paul Morphy’s style, wherein he was distinguished as “The Austrian Morphy,” he started gaining popularity that time and was able to win numerous international competitions.

Wilhelm Steinitz grew up from a low-income family; they were struggling hard in making ends meet; he was the youngest of a tailor’s thirteen sons.

In chess, it was his schoolmate who introduced to him the game of chess. He then somehow emulated the aggressiveness of Morphy’s style, not scared of sacrifices and taking unnecessary risks.

This type of style eventually prevented him from achieving great victories.

But…

He then changed his style to a more positional type of plays, it was more on understanding pawn formations, and this type of knowledge enabled him to defeat great players.

Steinitz is an active player, but when he misses following his principles, he can be easily be beaten by another solid chess player.

Let’s look at Wilhelm Steinitz chess game upset.

Steinitz Loses Chess Game

Giving Up Center Control Too Early

Wilhelm Steinitz does like to develop its pieces first in a game properly…

If he does seem to fail in doing the proper development, then he does make mistakes, and a strong player like Blackburne knows how to take advantage of it.

In this game, Steinitz was playing Black against Blackburne…

During this game, Steinitz was playing what chess experts call an anti-positional move, basically what this means is that there was no improvement with that kind of move.

Steinitz played Knight to e7, which seems like he was trying to give up the center.

A better move was Rook to e8, and then moving its pawn to d5 attacking the Whites center pawn together with Black’s Knight.

See chess position below:

best chess game steinitz

After White Queen moving to d2, Black moved it Knight to d7…

Again, chess experts were just shocked as to why Steinitz was retreating its Knight and only giving up the center of the board.

chess upset steinitz

It was better if Black looks for a move that can equalize the game, but instead, Steinitz opted for retreating its Knight.

See chess position below:

chess upset for wilhelm steinitz

Black’s game at this point was losing already, and everyone agreed that moving its Knight to c8 was just not right and was considered a losing move for Black.   Black was not giving any real attack or defense to White’s moves.   See chess position below:

Now White’s move of Queen to g5 made it all look hopeless for Black.

If you can look at Steinitz Knight was located, it was poorly placed in the 8th rank instead of having its minor pieces giving much-needed protection for the King for an impending attack.

See chess position below:

best chess upset

After, Queen h6 check by Blackburne, Steinitz should have resigned at this point.   He was checkmated, and it was grueling to see how Steinitz kept on giving up the central board with his Knight and keep on retreating on the board.   This was an upsetting loss to one of the greatest chess player of all time.  

(You may also like to read this article: 18 Important Chess Tactics You Should Know (With Examples))

Check out the chess game and notation below:

chess game upset

1. e4 e5 2. ♘f3 ♘c6 3. ♘c3 g6 4. d4 exd4 5. ♘xd4 ♗g7 6. ♗e3 ♘f6 7. ♗e2 O-O 8. O-O ♘e7 9. ♗f3 d6 10. ♕d2 ♘d7 11. ♗h6 ♘e5 12. ♗xg7 ♔xg7 13. ♗e2 f6 14. f4 ♘f7 15. ♖ad1 c6 16. ♗c4 ♗d7 17. ♗xf7 ♖xf7 18. f5 ♘c8 19. e5 fxe5 20. ♘e6+ ♗xe6 21. fxe6 ♖e7 22. ♕g5 ♕e8 23. ♖d3 ♖xe6 24. ♖h3 ♕e7 25. ♕h6+ ♔g8 26. ♖f8+ ♕xf8 27. ♕xh7#

3. Dr. Emanuel Lasker

He is a German Chess Player, born on December 24, 1868, in a Berlin suburb, Berlichen.

Well, he is known for becoming the longest reigning World Chess Champion for 27 years from 1894-1921, besides that Dr. Lasker also has a Ph. D. in mathematics from the University of Erlangen.

A well-respected professor of Mathematics at Heidelberg University in Germany. He has this idea of not giving all of his time to the game because he also devotes his time to mathematics and philosophy.

It was thought that Albert Einstein admired Lasker’s work and opinions on mathematics and philosophy.

In chess, Lasker’s brother was the one who introduced chess by showing him the moves at the age of 10. Never really showed that much interest in chess, he only played chess in competitions with very much less relevance.

But…

When he started taking chess seriously, he made significant victories beating top chess players during that time like Blackburne.

Lasker’s victories lead him to face Steinitz for the World Championship, wherein he won the chess game impressively and held that World Chess Championship for as long as twenty-seven years.

Although very talented and has a brilliant mind, Lasker suffered loses in his chess career...

Let’s check out Lasker’s chess game upset.

Lasker Loses in Chess Game

Poor Development of Chess Pieces

Lasker tends to be sloppy in the opening but become competent in the middle and end game…

In this game with Pillsbury where Lasker is already officially the World Champion, he showed exactly that type of gameplay in the opening.

Lasker was playing white against Pillsbury, and Pillsbury did not waste any time making sure that he will take advantage of Lasker’s poor chess pieces development.

After White’s black squared Bishop move to f4, Black captured White’s Knight f3.

Since the White Queen is no longer protecting the White Knight, Lasker captured the Bishop with its pawn, thus exposing Lasker’s White King on its kingside.

Some chess experts were saying that White is making poor development at this point of the game.

See chess position below:

best chess game upset

Another move that shows Lasker was not focusing on his chess pieces development like moving its Knight.

See chess position below:

And another move like below which chess experts were saying as White’s inferior chess move…

See chess position below:

lasker loses in chess game

After they exchanged Queen, and Black Knight captured Lasker’s Bishop, this is the point of the game where chess experts are saying that White should have resigned.

See chess position below:

chess game upset

Lasker had a bad game, and he was defeated seemingly very easy by Pillsbury.

It was a feeble development from his side; we do know that Lasker progress firmly in the middle game and end game but with this type of game that he just showed, Pillsbury was going to make sure he wins decisively.

Check out the chess game and notation below:

chess upset for lasker

1. e4 e5 2. ♘f3 ♘f6 3. ♘xe5 d6 4. ♘f3 ♘xe4 5. d4 d5 6. ♗d3 ♗e7 7. O-O ♘c6 8. ♖e1 ♗g4 9. c3 f5 10. ♕b3 O-O 11. ♗f4 ♗xf3 12. gxf3 ♘g5 13. ♔g2 ♕d7 14. ♕c2 ♘e6 15. ♗c1 ♗d6 16. ♘d2 ♖ae8 17. ♘f1 ♘exd4 18. ♕d1 ♖xe1 19. ♕xe1 ♘xf3 20. ♔xf3 f4 21. ♕d1 ♘e5+ 22. ♔e2 ♕g4+ 23. ♔d2 ♕xd1+ 24. ♔xd1 ♘xd3 25. ♔e2 ♘e5 26. f3 ♖e8 27. b3 ♘g4+ 28. ♔d2 ♘e3 29. ♗b2 ♘g2 30. h3 ♗c5 31. ♘h2 ♗f2 32. c4 dxc4 33. bxc4 h5

4. Jose Raoul Capablanca

He is a Cuban chess player, born in Havana on November 19, 1888.   He is considered to have an enormous innate chess skill because at the age of only twelve years old he became one of the best Cuban Chess Champion.  

Capablanca possesses a real natural chess talent, and he never really gave any importance to learning the theory of the game.   In chess, it was his father that gave him the inspiration to play chess, he saw his wealthy father playing chess with his friends, and that started his career in chess.  

It was noted that at the age of four years old Capablanca won his first game.   The only issue that some chess experts say about Capablanca’s style was that he never really had the theoretical knowledge of the opening and endgames of chess.  

He want to play chess purely with his skill and his chess intuitions.   With this lack of knowledge of chess theories, he suffered some significant chess losses during his time.   Let’s check out Capablanca’s chess game upsets.

Capablanca Loses in Chess Game

Immobilized Chess Pieces

Nobody doubted Capablanca’s excellent chess skills and he is one of the greatest chess players of all time.

But in some of his chess games, the lack of knowledge in opening theories caught up to him.

In this chess game, Capablanca was playing with another strong chess player, Dr. Lasker…

He played as Black in this game, and as we shall soon find out in this game, he will be making opening mistakes that Lasker was able to capitalize.

Early on the game, both chess players exchanged their Queens in the center of the board.

See chess position below:

best chess game capablanca

Nobody doubted Capablanca’s excellent chess skills and he is one of the greatest chess players of all time.

But in some of his chess games, the lack of knowledge in opening theories caught up to him.

In this chess game, Capablanca was playing with another strong chess player, Dr. Lasker…

He played as Black in this game, and as we shall soon find out in this game, he will be making opening mistakes that Lasker was able to capitalize.

Early on the game, both chess players exchanged their Queens in the center of the board.

See chess position below:

best chess game upset

After the exchange of the Queens, Capablanca was preparing to castle on the Kingside, by moving his Black Squared Bishop first.  

After analyzing the game, chess experts were suggesting that a better move would have been the White Squared Bishop to d7. For Black to castle on the Queenside instead of the Kingside.  

See chess position below:

chess upset for capablanca



During the 12th move of the game, it is evident that White has a better position.   White has two active Knights in the game, and Black’s Knight and white squared Bishop have nowhere to go.  


See chess position below:

chess upset for jose capablanca



White has an excellent outpost for its Knight, and Black has a terrible position with no chance of making any advanced move.  

Although Black is still trying to find a better position, Capablanca attempted to open up “a file” for its Rook to enter the game.  

See chess position below:

chess game upset for jose capablanca

Seeing White’s pawn is already slowly moving towards the Black’s Kingside, immediately Capablanca retreated his Rook.  

It was apparent that Black’s King needed protection on the Kingside that made Capablanca decide to abandon his attempt to do something on the “a file”…  

See chess position below:

chess upset

Finally, after 35 moves in the game, White made a brilliant move…   With that strong move, Black cannot do anything but let White win with the exchanges…

White was able to capture the Rook exchanging with its Knight with that excellent move.  

See chess position below:

capablanca loss the game

Capablanca’s loss in this game was because of his poor opening play, immobilizing his minor chess pieces versus White’s incredible positioning of its chess pieces.  

In the 42nd move of the game, Capablanca playing black resigned.   Capablanca knows how to get himself out of this type of situation but not in this game because Lasker was pretty much on top of his game at that time.  

Capablanca may have lose the game by inadequate knowledge of opening theories, as chess experts say.  

Check out the chess game and notation below:

chess game loss capablanca

1. e4 e5 2. ♘f3 ♘c6 3. ♗b5 a6 4. ♗xc6 dxc6 5. d4 exd4 6. ♕xd4 ♕xd4 7. ♘xd4 ♗d6 8. ♘c3 ♘e7 9. O-O O-O 10. f4 ♖e8 11. ♘b3 f6 12. f5 b6 13. ♗f4 ♗b7 14. ♗xd6 cxd6 15. ♘d4 ♖ad8 16. ♘e6 ♖d7 17. ♖ad1 ♘c8 18. ♖f2 b5 19. ♖fd2 ♖de7 20. b4 ♔f7 21. a3 ♗a8 22. ♔f2 ♖a7 23. g4 h6 24. ♖d3 a5 25. h4 axb4 26. axb4 ♖ae7 27. ♔f3 ♖g8 28. ♔f4 g6 29. ♖g3 g5+ 30. ♔f3 ♘b6 31. hxg5 hxg5 32. ♖h3 ♖d7 33. ♔g3 ♔e8 34. ♖dh1 ♗b7 35. e5 dxe5 36. ♘e4 ♘d5 37. ♘6c5 ♗c8 38. ♘xd7 ♗xd7 39. ♖h7 ♖f8 40. ♖a1 ♔d8 41. ♖a8+ ♗c8 42. ♘c5

5. Dr. Alexander Alekhine

He is a Russian and French chess player, born in Moscow on October 19, 1892.

Alekhine had a degree in law in St. Peterburg, but never really practiced law because of his passion for chess.

Considered to be the greatest chess player of all time, he won the Russian Amateur Championship at the age of 16 years old.

And at the age of 22, he was already one of the strongest chess players in the world.

Alekhine’s family was wealthy in Moscow, Russia, and his father was a landowner, a Marshal of the Nobility and a distinguished member of the Duma while Alekhine’s mother was the daughter of a wealthy industrialist.

In chess, it was his mother who introduced the game of chess.

Most chess experts admire Alekhine’s strength in the opening and amazing chess play in the middle game.

He looks at other Grandmasters at that time as efficient chess players but thought of them as lacking artistic appreciation for the game of chess.

Because Alekhine’s chess plays always confuses them, especially his deep opening innovations.

As great as Alekhine was in chess, he does have some losses in his chess life.

Let’s check out Alekhine’s chess game upsets.

Alekhine Loses in Chess Game

Playing With Inferior Moves

It was a World Chess Championship match in Holland, the year 1935…

Alekhine was playing Black against Dr. Euwe, and it was said that during this match Alekhine was drunk and did not gave serious attention to his opponent.

I believe that was true, but it does not matter because a loss is a loss.

As you will find out, Alekhine does play different opening tactics and even tries to surprise his opponent with his Bishop check to White King.

Chess experts believe that he did that purposely, knowing that he will lose a tempo with that move…

See chess position below:

chess upset alekhine

After Black Knight captures Knight on c3, Alekhine was aware of the White Bishop’s attacking the Black Bishop on b7…  

He has a good plan on trying to gain a positional advantage, but Euwe understood his intention. Instead, Euwe captured the Black Knight with his Bishop.  

See chess position below:

chess game upset



White played a smart move by moving its Pawn to d5.   This move blocks the Knight’s move to c6 and also attacking Black’s Pawn e6 at the same time, with its purpose to weaken pawn structure.  

See chess position below:

best player chess upset

Alekhine positioned his Bishop to make the exchange with White’s Bishop.  At this point of the game, Black felt White’s Bishop strong post that he is was not expecting to sacrifice three pawns in exchange for White’s Bishop.  


See chess position below:

chess game upset

White’s pawn structure has given Euwe a tremendous positional advantage.   And after Black’s move of Rook to f8,

White offered to make exchanges of Queen on e5.   Alekhine took White’s Queen, and it became more evident that Alekhine is making a lot of mistakes in his moves.  

With 46th and 47th moves of the game, Alekhine accepted defeat and resigned.   It was evident that Alekhine was playing with inferior moves, thus losing the game quite quickly.  

Check out the chess game and notation below:

chess upset alekhine

1. d4 e6 2. c4 f5 3. g3 ♗b4+ 4. ♗d2 ♗e7 5. ♗g2 ♘f6 6. ♘c3 O-O 7. ♘f3 ♘e4 8. O-O b6 9. ♕c2 ♗b7 10. ♘e5 ♘xc3 11. ♗xc3 ♗xg2 12. ♔xg2 ♕c8 13. d5 d6 14. ♘d3 e5 15. ♔h1 c6 16. ♕b3 ♔h8 17. f4 e4 18. ♘b4 c5 19. ♘c2 ♘d7 20. ♘e3 ♗f6 21. ♘xf5 ♗xc3 22. ♘xd6 ♕b8 23. ♘xe4 ♗f6 24. ♘d2 g5 25. e4 gxf4 26. gxf4 ♗d4 27. e5 ♕e8 28. e6 ♖g8 29. ♘f3 ♕g6 30. ♖g1 ♗xg1 31. ♖xg1 ♕f6 32. ♘g5 ♖g7 33. exd7 ♖xd7 34. ♕e3 ♖e7 35. ♘e6 ♖f8 36. ♕e5 ♕xe5 37. fxe5 ♖f5 38. ♖e1 h6 39. ♘d8 ♖f2 40. e6 ♖d2 41. ♘c6 ♖e8 42. e7 b5 43. ♘d8 ♔g7 44. ♘b7 ♔f6 45. ♖e6+ ♔g5 46. ♘d6 ♖xe7 47. ♘e4+

6. Robert James Fischer

He is an American Chess player, born in Chicago on March 9, 1934.

Robert James or Bobby Fischer was in high school for only two years in Brooklyn; it was evident that Bobby is more interested in playing chess than going to school.

Her mother Regina was able to him a scholarship to Brooklyn Community Woodward, and he attended other schools as well, but when he reached the age of 16, he dropped out of high school. He had this reason for not learning anything in school…

In chess, it was an instructional book that helped Bobby learn about chess, together with her sister Joan.

Joining the Manhattan Chess Club, he defeated older chess players at the age of twelve years old. Bobby won several chess championships and was considered to be a promising young chess prodigy during his time.

Bobby became famous when he was able to play for World Championship against Spassky. Later dubbed the “Match of the Century” in 1972. Bobby won the game of best of 24 matches.

It was Bobby who showed different types of psychological tactics and strong desires to defeat every opponent he meets.

But just like the other best chess player in this article, he is not unbeatable…

Let’s check out Fischer’s chess game upsets.

Fischer Loses in Chess Game

Missing A Draw Opportunity

This game happened in Skopje International Tournament in Yugoslavia.

Bobby likes to play chess with himself and studied a lot of chess games, one of the chess openings that he had a variation with is the Sicilian Defense.

He was playing White against Geller.

Bobby believed to have a solid chess play, but Geller came prepared…

In this early game, Bobby was playing well, and the variation in this move is very well known to Geller.

White and Black continue to develop their minor chess pieces.

See chess position below:

chess upset fischer

Geller’s 9th move showed aggressiveness and was looking to make rapid advancement of its Queen.

That lead Bobby to slow down and analyze a better move instead of rushing for an attack.

See chess position below:

bobby fischer chess upset

White’s moving Pawn to f5 is considered a blunder by the chess experts.

Because Black gave White no choice to give up a chess piece, by moving Black’s Pawn to b4.

See chess position below:

chess upset fischer

Chess experts were saying that Bobby has the option to perform a perpetual check against Geller with the move Rook to h5 and then sacrificing the Rook by capturing Black’s Pawn h7 check.  

After that move, White can check with the Queen and make a perpetual check.   But instead, Bobby played Pawn a3.  

See chess position below:

chess upset

Black’s only 23rd move, Bobby Fischer saw there was no escape for an immediate threat. He was forced to resign.   Again, White missed its opportunity twice to draw the game with a possible perpetual check.   It was a shocking and biggest chess upset for Bobby and one which he lose with only 23 moves in the game.  

Check out the chess game and notation below:

chess game upset

1. e4 c5 2. ♘f3 d6 3. d4 cxd4 4. ♘xd4 ♘f6 5. ♘c3 ♘c6 6. ♗c4 e6 7. ♗e3 ♗e7 8. ♗b3 O-O 9. ♕e2 ♕a5 10. O-O-O ♘xd4 11. ♗xd4 ♗d7 12. ♔b1 ♗c6 13. f4 ♖ad8 14. ♖hf1 b5 15. f5 b4 16. fxe6 bxc3 17. exf7+ ♔h8 18. ♖f5 ♕b4 19. ♕f1 ♘xe4 20. a3 ♕b7 21. ♕f4 ♗a4 22. ♕g4 ♗f6 23. ♖xf6 ♗xb3

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Wrapping Up

Those are just some of the best chess players that I consider to be the best in the game…

As you have witnessed, they are beatable, but they can never really be classified as an average chess player. I believe they can easily beat me even if they don’t have both their Rooks… 🙂

I just wanted to share this article to you to show you that losing does not mean you cannot be great in chess.

There will always be a next time, and losing in a chess game will make you become a stronger chess player.

I do hope this article was able to inspire you in some ways, and I hope you keep on improving your chess tactics and strategies to win more games.

I know most of you consider some of this chess players as heroes (because I do too), use them as your inspiration to be great at chess and never give up learning or teaching your kids how to play chess.

If you do have some stories to share about some of the biggest upsets of famous chess Grandmasters, please do share them in the comments below.

Have fun learning chess! 🙂

Gary Flores

Hi there! I'm a dad with kids who loves to learn how to play chess by learning online - also, this is my way of refreshing my knowledge about this game of tactics & strategy. I created chessdelights.com to inspire people who are also learning, re-learning or teaching their kids the game of chess.

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