The Baltimore Orioles selected Gillispie in the ninth round,with the 258th overall selection,of the 2019 Major League Baseball draft.[2] He made his professional debut with the Low–A Aberdeen IronBirds,recording a 1.77 ERA with 21 strikeouts over 14 appearances. Gillispie did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.[3]
Gillispie returned to Aberdeen in 2021,now a High–A affiliate,and posted a 4–8 record and 4.97 ERA with 78 strikeouts across 21 games (12 starts).[4] He returned to Aberdeen for a third season in 2022,compiling an 8–5 record and 3.79 ERA with 113 strikeouts over 25 appearances (14 starts).[5]
Gillispie spent the 2023 campaign with the Double–A Bowie Baysox. In 27 games (14 starts),he accumulated a 7–4 record and 3.89 ERA with 99 strikeouts and 2 saves across 115+2⁄3 innings pitched.[6]
Cleveland Guardians
On December 6, 2023, the Cleveland Guardians selected Gillispie from the Orioles in the minor league phase of the Rule 5 draft.[7] Gillispie began the 2024 season with the Triple-AColumbus Clippers. On August 4, 2024, Gillispie was selected to the 40-man roster and promoted to the major leagues for the first time.[8] In 3 appearances during his rookie campaign, he posted a 2.25 ERA with 8 strikeouts across 8 innings of work. Gillispie was designated for assignment by Cleveland on November 19.[9][10] On November 22, the Guardians non–tendered Gillispie, making him a free agent.[11]
Miami Marlins
On November 29, 2024, Gillispie signed a one–year, major league contract with the Atlanta Braves.[12] Gillispie was designated for assignment by the Braves on January 23, 2025.[13]
On January 28, 2025, the Miami Marlins claimed Gillispie off of waivers.[14] After making Miami's Opening Day roster, he made six starts for the team, struggling to an 0-3 record and 8.65 ERA with 23 strikeouts over 26 innings of work. Gillispie was designated for assignment by the Marlins following the promotion of Robinson Piña on June 19.[15]
Minnesota Twins
On June 23, 2025, Gillispie was claimed off waivers by the Minnesota Twins.[16] In four appearances (three starts) for the Triple-A St. Paul Saints, he struggled to a 1-1 record and 14.49 ERA with six strikeouts across 13+2⁄3 innings pitched. Gillispie was designated for assignment by the Twins on July 28.[17] He cleared waivers and was sent outright to Triple-A St. Paul on July 30.[18]
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