Round 4 of Pittsburgh Chess Club tournament: the agony of losing a won game against the difficult opponent

After round 3 last week of the current Pittsburgh Chess Club Tuesday night tournament, I noted that I was going to face a difficult opponent in round 4.

Well, I lost my game against him tonight, after four hours of play (we were the last game to finish):

White resigned

This is the first chess game I’ve reported on in this blog in which I lost!

What lessons from losing?!

What makes this loss particularly agonizing is that I had an advantage for a long time in the game (and had a win at one point), and entered an endgame a solid Pawn up such that if I were playing for a draw, there would not be any way to fail, but instead I made error after error until I lost. Even worse, I actually had a drawn position just moves before I resigned.

Here’s what happened.

The complete annotated game

At your convenience, you can enjoy playing over the game with my annotations, including diagrams.


I was faced with the psychological challenge of playing a “difficult opponent”, which I define as someone who I have a bad score against. I had lost one game to my opponent and drawn one game that I almost deserved to lose.

As White, I had the choice of playing into one of his favorite openings or avoiding it. I ended up doing something halfway: allowing his opening but choosing a different way of responding to it. I did this with the expectation of reaching a certain kind of middle game that would be solid for me as White: a Ruy Lopez kind of position.

Overview of my game

The opening

My opponent again tried to enter the Philidor Defense through a Pirc Defense move order. I varied with the quiet Bd3 variation in order to bolster my e4 and d4 center with c3.

I made some inaccuracies in the opening by not playing an early Be3 that would have guaranteed a safe advantage.

Still, I achieved a solid position:


The middle

Then, out of the blue, my opponent creatively embarked on a Pawn sacrifice.

Unsound sacrifice by Black

The way he played it was actually completely unsound, such that if I had taken the time to find the best moves, I would have won. But it was a creative idea: it was meant to be a positional sacrifice, choosing to lose a Pawn in order to gain the advantage of the two Bishops and better development. It should not have worked, however.

White is a solid Pawn up but lost the two Bishops

His bluff worked, and I fell into a position in which although I was one Pawn up and had the advantage, it was not going to be trivial to actually win rather than draw.

After I finished developing my pieces, I immediately traded into an endgame in which I was a Pawn up and objectively had no chance of losing.

Traded off

The end

Here’s where things got weird. When I realized that I did not have much of a chance of winning, I started dreaming up strange attacks that ended up not working at all. I started losing Pawns, my Knight ended up much worse than his Bishop (thereby justifying his positional sacrifice in the first place to get the Bishop), and I was dead lost.

White in bad shape

Then magically, at some point he started playing poorly, to the point at which I finally achieved a drawn position!

Drawn position

But at that very moment, I played an incomprehensibly terrible move, and immediately after that, realized I was lost. The rest of the game was meaningless given that. I resigned when he was about to Queen a Pawn.

White resigned

Lessons learned

What next?

Well, I now lose the lead in the tournament. I don’t know yet whom I’ll be playing in round 5. I have probably lost the chance to win this tournament, as a result of my loss, but I intend to play well during the final two rounds!


It’s always tough to lose a chess game. It’s especially hard when you identify the kinds of errors you made and what you could have done differently and thought about but decided poorly.

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