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You play against yourself, using your own opening repertoire. Thus by playing both White and Black, you reach positions that should be fairly equal, and then you continue to play both sides, obviously knowing each sides' plans. Should the game always end in a draw? How often is White expected to win?

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No.

When you are playing seriously against yourself, you still have to commit to moves. After making the move you start analysing again and see things you previously have not seen, and you may discover an error in the moves you have already made and the game becomes a win for one of the sides you play.

Or you may find a winning way without really catching an error in the previous moves.

Note that there are no secret plans in chess, the full truth is always on the board. It is up to you to read the board and draw the best consequences of that reading.

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  • What if you are a very strong player, say a grandmaster who excels in calculation? Same answer still?
    – prestokeys
    Apr 7, 2015 at 15:52
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    Yes, still the same answer. Even a grandmaster is far from playing like the Goddess of Chess. Machines can do much more calculations than grandmasters and still have decisive games against themselves.
    – Sir Cornflakes
    Apr 7, 2015 at 16:07
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I could probably beat myself because sooner or later I'd make a blunder that I'd spot the second I'd played it. That would allow me to exploit the blunder with the other pieces.

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It depends on how good you are. (The worse you are, the more likely that you could make a mistake as one side and then later see how to exploit it as the other.) Almost all skilled players believe that the game of chess is a draw given best play by both sides.

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  • I'd clarify that as, "Almost all skilled players believe that the game of chess is a draw given perfect play by both sides." However, perfect play is never possible. We can only do our best, and there are many fine and distinct levels between each player's best and the ever-evolving board combinations: Someone will win, even if it's the same person.
    – Grey Dog
    Apr 7, 2015 at 23:27
  • By "best play" I indeed meant "perfect play"; otherwise some other play would be better and it wouldn't be best.
    – dfan
    Apr 8, 2015 at 0:14
  • While players statistically play predictably between the various strengths, any one game has a player playing within a distribution of his average power. So, even if he's say 2200, he should statistically play one side just a little better than another by randomness, because the odds that both sides will play the same exact rating between 2100 and 2300 is very, very small. Of course, that's assuming the rating system is perfect (it's not, but it is good, and in this case many confounding factors are removed by playing self against self).
    – Edwin Buck
    Apr 8, 2015 at 3:01
  • @dfan If perfect play was known to lead to a specific outcome, then the game of chess would be "solved" from a game theory point of view. As far as I know, it's not solved, at least not yet.
    – Edwin Buck
    Apr 8, 2015 at 3:02
  • @EdwinBuck I agree with your first comment; that's why I said "It depends how good you are" - bad players will have more decisive results than good players, who will have more decisive results than perfect players.
    – dfan
    Apr 8, 2015 at 12:04

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