A native of Baytown, Texas, just outside Houston, Derrick Cherry returns for his second season with the Winnipeg Goldeyes in 2026 after a strong debut campaign and another busy offseason on the international stage.

Derrick began his college career at the University of Houston as a two-way player, contributing both on the mound and at the plate during his first three seasons. He eventually transitioned into a full-time pitching role before transferring to McNeese State University to complete his collegiate career.

After college, Derrick joined the Oakland Ballers for the 2024 season and made an immediate impression in his first year of professional baseball. He later finished the season with the Rocky Mountain Vibes before signing with Winnipeg ahead of 2025. In his first season with the Goldeyes, Derrick became a reliable part of the bullpen, working 66 innings over 40 appearances while striking out 62 batters and posting a 4.09 ERA.

His offseason took him halfway around the world. Derrick travelled to China to pitch for the Shenzhen Bluesox in the inaugural Chinese Professional Baseball Spring League, helping the club capture the championship during the 12-week season.

Only weeks later, he joined Winnipeg teammate Max Murphy and the Kane County Cougars at the Baseball Champions League Americas in Mexico City. Derrick appeared in four games during the tournament and delivered a strong outing against Diablos Rojos del México, whose roster featured numerous Mexican League standouts and former Major Leaguers. Kane County completed a perfect 5-0 run to the championship, giving Derrick back-to-back international titles in consecutive months.

That stretch added another chapter to a professional career that has already taken Derrick from the Pioneer League to Winnipeg and onto championship teams in both Asia and Mexico.