I never understood how that game works. If it was a game of chance, then Data had as many chances to win as anyone else could. If it was a strategy game where there was an element of chance anywhere along the line, then it didn't matter if Data played the game perfectly, he could still have lost, and it wouldn't have been computer error.
If the game was strictly a mathematically rigid battle of strategy, without any chance involved in the game, then Data failing to win both time, is in fact a computer error, and makes his hardware or programming faulty somewhere along the line.
I got the impression it was the starship equivalent to Risk
. Not quite mathmatically perfect as Chess and requiring a great deal more judging your opponent's decisions and how to deal with them.
Which, having no emotions, Data would SUCK at.