After failed attempts to put a team in Kansas City in the Union Association in 1884, which by some accounts was barely a major league and the National League in 1886, the American Association made their move in 1888. Like their two predecessors the team was called the Kansas City Cowboys.

The Cowboys struggled in their first season, as they changed managers twice. Dave Rowe started the season 14-36, he was followed by Sam Barkley doing slightly better at 21-36 while Bill Watkins led them to an 8-17 mark over the final 25 games.

In total Kanas City finished the season with a record of 43-89, at the bottom of the American Association. Despite the struggles there were some highlights as Henry Porter no hit the Baltimore Orioles on June 6th.

A week later, Sam Barkley hit for the cycle against the Cincinnati Red Stockings. Jumbo Davis was the Cowboys leading hitter with a .

267 average, while Porter posted an 18-37 record on the mound. On other player of note was Billy Hamilton, who made his professional debut, hitting .

264 with 19 steals in 35 games. Hamilton would be the leading base stealer in the 19th century, swiping 914 bases.