I've done similar things with Chessmaster 9000 personalities. Some of them I had to play around 100 times before I beat them. The highest I've gotten is "Jade". It isn't very hard to draw, but I haven't beaten it yet. All before "Jade" I have beaten at least once.
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I rember when I was younger I had a old version of chessmater for the gameboy and the AI (Computer opponents) were in a list me not knowing the list was just random (ratings weren't told) I told myself I would go through the list trying to beat the computers thinking the list was from easiest to hardest and to not go on until I beat (draws didnt't matter) the current level.
beat the 1st one on my first try. beat the 2nd on my 2nd try. beat the 3rd on my 4th try. beat the 4th on my 12th try!!! and after that I relized these computers can't be in order so I stopped the whole thing for a while. about a year ago I still (still do now) having the program I decided to check the ratings of all the AI the 1st was estimated barely above 700 and the 2nd and 3rd were 900ish (2nd) and 1300ish (3rd) and the 4th estimated about 2100!!! and it actually felt good knowing this just by reializing how string of a opponent I'd beaten during such a inexperiance time when I played.
the question is have you had a similar experiance were you beaten someone or something by determination in playing them over and over as I did ??
I personally didn't even play anyone else but that computer when I was trying to beat it believeing that playing anyone else would only make me forget about how I loss against the one I was trying to beat. Also the games were all bloody meaning no draws.