The team began the 1888 season with part-time outfielderDave Rowe as their player-manager. He was released from the team after beginning the season with a win–loss record of 14–36 though 50 games.[4] He was replaced with second basemanSam Barkley, who did not improve the team's play, winning 22 of the next 58 games.[4] He was replaced with non-playing managerBill Watkins, who finished the season.[4] Although the Cowboys completed their initial season in last place out of the league's eight teams, there were notable player achievements; on June 6, Henry Porter threw a no-hitter, and on June 13, Barkley hit for the cycle.[4][5][6]
The franchise's only future Hall of Fame player, "Slidin' Billy" Hamilton, began his career as a part-time outfielder in 1888, and was their starting right fielder in 1889.[7][8] He is the franchise's all-time leader in runs scored, bases on balls, and stolen bases.[9] With Watkins as the team's manager in 1889, the team improved their win–loss record to 55–82, with two ties, finishing seventh among the league's eight teams.[10][11] On November 15, 1889, the Cowboys submitted their resignation from the AA and joined the Western Association as the Kansas City Blues for the 1890 season.[12]