[1] He made his professional debut with the rookie–level Elizabethton Twins, making three scoreless appearances in his inaugural campaign.

Headrick did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.

[2] In 2021, he spent the majority of the year with the Single–A Fort Myers Mighty Mussels, also making a single start for the rookie–level Florida Complex League Twins.

In 15 games (14 starts) for Fort Myers, Headrick logged a 3.82 ERA with 86 strikeouts in 61+1⁄3 innings pitched.

[3] In 2022, Headrick made 25 appearances (23 starts) split between the High–A Cedar Rapids Kernels and the Double–A Wichita Wind Surge.