He has previously played in Major League Baseball (MLB) for the San Francisco Giants, Boston Red Sox, and Los Angeles Dodgers.

For the Missouri State Bears baseball team, Kickham had a 4–9 record with a 5.25 ERA and 103 strikeouts, in 96 innings spanning 15 games.

In 2012, he was promoted to the Double-A Richmond Flying Squirrels, where he posted an 11–10 record and a 3.05 earned run average (ERA) in 28 games.

[6] With the Giants in 2013, Kickham made a total of 12 appearances (three starts), accruing an 0–3 record with 10.16 ERA and 29 strikeouts in 28+1⁄3 innings pitched.

[15] Kickham signed with the Kansas City T-Bones of the American Association of Independent Professional Baseball on June 26, 2016.

[16] In 27 games (25 starts) split between the Triple–A New Orleans Baby Cakes and Double–A Jacksonville Jumbo Shrimp, he posted a cumulative 8–10 record and 3.65 ERA with 119 strikeouts in 145+2⁄3 innings pitched.

In 20 games split between New Orleans, Jacksonville, and the rookie–level Gulf Coast League Marlins, he accumulated a 3.64 ERA with 38 strikeouts in 42.0 innings of work.

[18] On November 16, 2018, Kickham again re-signed with Miami to a new minor league contract, and was invited to spring training.

[20] On December 20, 2019, the Boston Red Sox signed Kickham to a minor league deal and invited him to spring training.

[23] Kickham recorded his first MLB win on September 5, when he pitched two innings of scoreless relief and the Red Sox came back to defeat the Toronto Blue Jays with two ninth-inning runs.

[24] Overall with the 2020 Red Sox, Kickham appeared in five games (two starts), compiling a 1–1 record with 8.31 ERA and 16 strikeouts in 13 innings pitched.

[25] On January 8, 2021, the Los Angeles Dodgers organization signed Kickham to a minor league contract.

[36] On March 14, 2024, Kickham signed with the Hagerstown Flying Boxcars of the Atlantic League of Professional Baseball.