The strategy is behind when it wins 49 trades or fewer out of 100. With a win rate of 0.55, that probability is about 13.5%. It finishes exactly level, 50 wins and 50 losses, another 4.8% of the time.
After 400 trades it is behind when it wins 199 or fewer. That probability falls to about 2.0%.
A normal approximation gets close. Over 100 trades the expected number of wins is 55, with a standard deviation of about 5, so finishing level at 50 wins sits 1 standard deviation below the mean. Over 400 trades the expected lead is four times larger and the standard deviation only twice as large, so level sits 2 standard deviations out.
A real edge loses money over 100 trades about one time in seven. This is why we judge strategies over long samples and never on a good month.