[1] Crawford made his professional debut in 2017, making a single start with the Class A Short Season Lowell Spinners of the New York–Penn League.

[3] He did not pitch professionally during 2020,[2] due to cancellation of the minor-league season, and had surgery mid-year to remove bone spurs in his elbow.

[8] Between Worcester and Portland, Crawford made 20 minor-league appearances (19 starts), pitching to a 6–6 record with 4.28 ERA.

[18] Overall with the Red Sox during 2022, Crawford compiled a 3–6 record in 21 games (12 starts) with a 5.47 ERA while striking out 77 batters in 77+1⁄3 innings.

[19] Crawford began the 2023 season with Boston,[20] and was optioned to Worcester on April 11 when Garrett Whitlock was activated from the injured list.

[23] On May 6, Crawford was ejected from a game and fined for not leaving the field after the conclusion of the national anthem despite an umpire's warning.

Philadelphia Phillies pitcher Matt Strahm was also ejected for taking part in the "anthem standoff" where players compete to leave the field last.

The ejection and subsequent fine was largely due to the introduction of the pitch clock, intended to speed up the game and prevent unnecessary delays.