Drew Stengren hails from Fox River Grove, Illinois, where he helped his high school, Cary‑Grove, win a regional championship in 2019. The catcher went on to play collegiately at Central Michigan University from 2021–24, appearing in 118 games for the Chippewas. During that span, he committed only six errors, walked as often as he struck out, and posted a .321 on‑base percentage. 

After his college career, Stengren signed with the Joliet Slammers of the Frontier League. In his rookie season, he recorded a .276 batting average, a .360 OBP, and a .995 fielding percentage across 50 games. In 2025, he appeared in 34 games for Joliet, hitting .184 with a .300 OBP and tallying 16 walks to 15 strikeouts.