It would be 39 * 500 = 19500. Now subtract the three losses, playing it the way JM says to and buy 3 points, which on average is -180 odds per game, and your losses for the three series would be 3 * (-10,476) = -31,428. Playing to win 500 on each series would have netted you (-11920). I would concur, a terrible season. A single three game chase loss, looking to win 500 = (-10476)