ペンサコーラ・ブルーワフーズ
Diplan was designated for assignment on July 29, 2019 following the acquisition of Jordan Lyles. He was traded to the Minnesota Twins for cash on July 31, 2019. Between Biloxi and the Pensacola Blue Wahoos, Diplan went 3–5 with a 4.85 ERA in 68.2 innings in 2019. On September 14, 2019, Diplan was designated for assignment. He was claimed by the Detroit Tigers on September 16.