The Biggest Chess Upsets of All Time
Let me know in the comments if you can guess the player in the right of the thumbnail based on the game. ©Canva 2023

The Biggest Chess Upsets of All Time

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An upset in a competition occurs when the favorite (or the team/competitor expected to win) loses to the underdog. In chess this is no different, since of course, the higher rated player doesn't always win in a chess match. In fact, we saw living testimony to this very recently when Hans Niemann defeated Magnus Carlsen in the 2022 Sinquefield Cup and numerous cheating allegations arose as a result. Regardless, not every upset has ended in controversy, and today we'll be looking at the five most impressive/important upsets in chess history. 


Table of Contents 


#5: Passing on the Torch 

Hou Yifan and Judit Polgar before their historic Round 7 game in the 2012 Tradewise Gibraltar Chess Festival. ©ChessBase

The year was 2012. The strongest rated female chess player of all-time, Judit Polgar, was paired against the 25th seed of the Gibraltar Masters, Hou Yifan. Now you may be wondering, what's so significant about this matchup? Well unlike the top of the world rankings who had recently had a change when Magnus Carlsen skyrocketed up the list in 2009, Judit Polgar had remained atop the women's list for the past two decades.

As a result, Hou Yifan, at just 17 years old and holding a "mere" FIDE rating of 2605 (as opposed to Polgar's record-breaking 2710) was widely expected to lose. However, Hou had put on a stellar performance up to this moment in the tournament, with a score of 4.5/6, the same as Polgar's current record. Additionally, her performance would have her break the barrier into the world's top 100 players, where she would ironically join Polgar as one of the two female players in that list. 

Playing black against the strongest woman player in history was the daunting task laid before China's up and coming player. The two had never faced each other in competitive play before, due in part to Judit Polgar's lack of participation in open tournaments in recent years. The stakes were high, so Hou prepared herself for one of the most challenging battles of her early career.

Hou Yifan's upset of Judit Polgar was shocking to say the least. She ended up tying for first in the Gibraltar Masters alongside English GM Nigel Short. This was an important game because it marked the passing of the torch from Polgar to Yifan in the field of professional women's chess. Hou is currently regarded as the second most dominant female chess player in history despite being only 29. She boasts four Women's World Championship titles along her numerous accolades and accomplishments.


#4: Caro-Kann Goes Haywire 

IM Rahul Shetty in a 2018 picture beside his various chess awards. ©MumbaiMirror

The next game was played in the second round of the Canadian Open 2006. Russian-Canadian grandmaster Evgeny Bareev was black against Indian international master Rahul Shetty. Evgeny Bareev was one of the hottest players at the time, winning the prestigious Wijk aan Zee Tata Steel tournament and becoming one of the candidates for the World Championship, both in 2002. He later reached his peak rating and became the #4 player in the world in 2003. 

Meanwhile, Rahul Shetty was a relatively unknown player who hadn't played in too many notable tournaments at this point. However, he had begun the tournament 1-0 like Bareev, and was now playing Bareev himself with the white pieces. With a 400 elo difference between the two players, Bareev didn't have high chances of winning. 

This loss was exacerbated by the fact that Bareev's chances were spoiled by a middlegame mistake right out of the opening. Just two moves out of opening theory and Canada's strongest contemporary grandmaster had already misplayed his position. While this remains as Shetty's most prominent victory to this day, he has since had solid results across competitive play, and finished in the top 10 in the Canadian Open after facing Bareev.

#3: The London System is Trash
FM Shahriyar Rahmanov posing with his third place medal from an online Azerbaijan chess tournament. ©Facebook

The 2008 President's Cup kicked off with a round 1 matchup between eight-time Dutch champion Loek van Wely and future FM Shahriyar Rahmanov who was 2100 elo at the time. Only 18 at the time of their game, Rahmanov showed promise, but was unable to keep up with some of his young peers. Furthermore, he was paired against one of the strongest participants in the competition in round 1, with the black pieces. Certainly no easy task before him, but Rahmanov had waited for this moment and believed he stood a chance.
That truly may have been Loek van Wely's worst game of the early 21st century. According to Chess.com's analysis feature, the two players combined for a total of 15 blunders/mistakes. Rahmanov had an accuracy of 73% and a 2000 elo performance, and van Wely had an accuracy of 67% and a mere 1800 performance. Then van Wely blundered a mate-in-4 which sealed his doom versus the FM 500 elo his inferior.

#2: Kasparov's Worst Game 
GM Alexander Huzman, the top seed at the 2014 Gideon Japhet Memorial Open.

The European Club Cup was a 90/30, seven round, Swiss, team tournament held in Crete, Greece. 45 clubs representing 27 total countries were entered in the competition with Team Paris eventually winning in the end. In round 6 Israel's GM Alexander Huzman had the privilege of facing one of the greatest players to ever play on the 64 squares in Garry Kasparov.

This game was unlike the other entries in this list since both players were grandmasters. However, Kasparov still had a 300 point advantage, informally categorizing him as a "super" GM. Moreover, it's safe to say that Garry Kasparov is one of the best World Champions and one of the greatest, most dominant players in history. Scoring an upset against Kasparov would be the highlight of Huzman's career so far.

This wound up being Huzman's highest ranked victory ever, and Kasparov's worst loss of his post World Champion career in terms of point differential. Huzman was able to exploit a rare blunder from the Beast of Baku and beat Kasparov at one of his specialty openings.


#1: Defeated by the Russian in Russia

Olivier Touzane (right) plays Etienne Bacrot (left) in 2017. ©Twitter

In 2001, both IM Olivier Touzane and former World Champion GM Viswanathan Anand were registered for the FIDE World Championship Knockout, a 128 person knockout-style event that would run until there were two remaining players for the finals. These two players would then compete 1v1 for a shot at the FIDE World Champion title (not to be confused with the classical WC title). However, FIDE had recently changed its format to 90/30, a time control that veterans like Anand weren't familiar with.


Those who spectated this game said that Vishy simply played too fast and blundered. Perhaps this was due to the new time control rules implemented by FIDE, perhaps it was due to overconfidence. Regardless, this was an astonishing upset. Earlier that day, Vishy was one of the favorites to win the entire tournament, and he instead started off with a loss to an IM -400 his rating. Viswanathan did win his next game and advanced to round 2, but this was a massive victory for his young opponent. 


Conclusion:

As always, thanks so much for reading. I hope you enjoyed/learned something from this post, and if you did make sure to leave a comment since I appreciate all the feedback I receive. I'd like to post one more OTB recap before the end of the year (especially considering I haven't played OTB since July), so if I play in any events I'll definitely post those. Y'all can expect at least one more post this month and probably one in December to wrap up a great year of blogging. Thanks again for reading. Until next time,

-Nimzo