In all, he managed 11 seasons in the majors, compiling a record of 351 wins and 502 losses, winning one championship in 1890 with the Louisville Colonels of the American Association. Chapman took part in the pre-modern era World Series by managing his team in the 1890 World Series, the seventh of eight held prior to the first modern Series in 1903. The team faced the Brooklyn Bridegrooms of the National League that would be held as a best-of-seven series. Brooklyn won the first two games before the third game ended in an eight inning tie. Louisville won two out of the next three to force a seventh game amidst worsening weather conditions. Chapman and Brooklyn manager Bill McGunnigle agreed that the October 28 game would be the last one held, although it was stated that if Louisville won the game and tied the series that they would meet again in the following spring to determine the true winner. Louisville won 6-2, but the agreement between the AA and the NL floundered in the winter, meaning that no true winner of the 1890 Series was awarded that year.
Chapman's nickname was "Death to Flying Things", although fellow major leaguer Bob Ferguson had also been given the nickname. Chapman died in Brooklyn at the age of 73, and he is interred at Green-Wood Cemetery.

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