[2] Willingham did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.
[4] On August 14, 2021, Willingham combined with Gilberto Chu and Leif Strom to no–hit the Salem Red Sox, the first no-hitter thrown in Fredericksburg history.
In 6 contests for Wilmington, Willingham struggled to a 14.54 ERA with 14 strikeouts and 6 walks across 13.0 innings, and was returned to Fredericksburg shortly thereafter.
[6][7] Willingham spent the 2022 season with High–A Wilmington, making 29 appearances and registering a 3.41 ERA with 40 strikeouts and 3 saves in 34+1⁄3 innings pitched.
[8] He began the 2023 season with the Double–A Harrisburg Senators, and logged 14 strikeouts and 5 saves in 10+2⁄3 scoreless innings pitched across 10 contests.