Holiday Invitational Round#1 – A drawish chess endgame

Losing a won chess game

Game #39 – Why understanding chess endgames is so important

I started playing in my personalized 10-round tournament against Chessmaster XI‘s “Turk” personality. Like I mentioned in a previous post, the game was played under tournament conditions except for the time restrictions. I used a physical chess board and wrote down all my moves on a chess scoresheet (see image below).

Holiday Invitational Round#1 - A drawish chess endgame

This was the first game of the match and I played with the white pieces. I had the advantage early, seizing key squares, doubling rooks on the open f-file and having things go my way well into the middlegame.

I captured Black’s c5 pawn to secure a winning advantage — Black had no compensation for the lost pawn. After several more trades, I arrived at a winning chess endgame. This is where I screwed up. Instead of advancing my pawns early in the middlegame, I squandered my time with passive moves that didn’t improve my position.

Whenever you are up a pawn in a chess endgame, it is important to begin to advance your pawn majority down the board. I didn’t do this and it cost me a win. Still, a draw is better than a loss but it’s important for me to be able to convert a winning chess endgame.

Paul H. – Chessmaster XI (Turk)
Scotch Four Knights Defense [C47]
Holiday Invitational, Round 1

Post-game analysis

Putting pieces on good squares. Playing chess is about checkmating your opponent’s king. This is the ultimate objective but it doesn’t happen so easily. Strong players won’t fall for simple mating attacks. They see what you are planning and defend against it. Chess, just like in real war, is a game of controlling territory. In war, the more territory you own, the more operations you can perform against your enemy. In this game, my superior control of the board coupled with the placement of my pieces is what gave me such an advantage early in the game.

What I failed to do is to continue to grab more space by inching my pawns forward. This is an important lesson for the amateur reader to understand. If you can’t come up with a plan, try to improve your position. For me, that would have been playing a move like b4, establishing more space and limiting my opponents mobility.

Think about a chess endgame in the middle game. The importance of learning endgame play can not be underscored enough. However, little has been written on transitioning a chess game form the middlegame to the ending. In this game, winning the c5 pawn on move 18 was the first sign that I should be thinking about an ending. Look at the position below.

Holiday Invitational Round#1 - A drawish chess endgame
Position after 23…Rd8. White is winning.

Playing b4 here is the beginning of the end for Black. I have a 4 vs 3 pawn majority on the queenside that is difficult to stop. The priority here is to trade queens and start advancing pawns to a queening square.

Passive moves, the bane of an amateur player’s existence. Moves that don’t improve your position or don’t fulfill a plan are simply wasted moves. My series of queen moves, Qc5-c4-c3 did nothing to help my position. I can tell you why too. For some reason, I was supremely focused on mating the black king. This single-minded fixation is a problem for me but I am working on it. Good players shift their strategy – if one plan doesn’t work, they switch to another. In my case, I am forcing a mating sequence that does not exist.

Launching a mating attack from the above diagram is not possible — not at this late stage in the game anyway. Instead, my focus should have been on my extra pawn. The plan should have been to force trades, centralize my king and begin to advance my pawns.


Getting a draw in a won game is frustrating but it’s better than a loss. The transition from middlegame to a chess endgame is a difficult one. It requires a level of awareness and objectivity that most amateur players lack. For future games, I will to remember to focus on my strengths and not get distracted by delusional ideas that have no chance of working.

Holiday Invitational Round#1 - A drawish chess endgame