[4] The Paints play in the Prospect League's Eastern Conference – Northeast Division along with the Champion City Kings, Johnstown Mill Rats, and Lafayette Aviators.

Two teams, the West Virginia Coal Sox and the Tri-State Tomahawks, did not complete the season as the league struggled with stability.

[12] The Paints were led at this time by the stellar hitting of Gator McBride, a former Atlanta Braves farmhand, who came to Chillicothe and would finish his Frontier League career with a .423 BA, .758 slugging percentage, 27 homers, and 111 RBI.

[13][14] His career was cut short by injuries sustained in an automobile accident in February 2000, forcing him into retirement.

[15][16][17] The Paints returned to the Frontier League championship in 2001 with a division-winning 51-31 (.607) record, but were upset by the Richmond Roosters 2–0 in the series.

[28][29] Following the 2008 season, the ownership announced that they would leave the Frontier League, becoming an amateur collegiate summer baseball team.

[30][31][32] The Paints are represented in the Frontier League Hall of Fame by owner Dr. Chris Hanners, 1B Scott Pinoni, infielder Mitch House, OF Willie Edwards, pitcher Bobby Chandler, OF Gator McBride, and 3B Travis Garcia.

In 2010, the Paints won their first Prospect League championship against the Danville Dans on an 11th inning walk off home run by Ian Nielsen.

Trailing 2–1 in the middle of the game, Trey Smith hit a grand slam to put Chillicothe in the lead 5–2, the eventual final score.