The Spiders' first manager was Jimmy Williams, who managed the team as the Cleveland Blues in 1887 and the beginning of the 1888 season. Williams managed a total of 197 games for the team, winning just 59 against 136 losses for a winning percentage of .303. This low winning percentage would prove one of the best in team history.
After Tom Loftus, Gus Schmelz and Robert Leadley handled the managerial duties from the middle of the 1888 season though the middle of the 1891 season, first basemanPatsy Tebeau became the Spiders' player-manager 69 games into the 1891 season. Tebeau would manage the Spiders through the end of the 1898 season. Tebeau holds the Spiders' records for most games managed, with 1040, most wins as manager, with 579, most losses as manager, with 436, and highest winning percentage, with .570. Tebeau is in fact the only Spiders' manager to have won more games than he lost. In 1894 and 1895, Tebeau had the distinction of managing his brother George Tebeau, who played outfield and first base for the team.
In 1899, third basemanLave Cross became the Spiders' player-manager. The Spiders won just 8 of 38 games under Cross, for a winning percentage of just .211, before Cross was replaced as player-manager by second basemanJoe Quinn. The Spiders performed even more poorly under Quinn, winning just 12 games and losing 104, for a winning percentage of .103. The Spiders' 1899 record of 20 wins and 134 losses under Cross and Quinn is the worst in professional baseball history, and the team was dropped from the Major Leagues after the season.