| 06/04/2019 |
Drafted by the Minnesota Twins in the 9th round of the 2019 MLB June Amateur Draft from Illinois State University (Normal, IL). |
| 02/11/2025 |
New York Yankees claimed LHP Brent Headrick off waivers from Minnesota Twins. |
| 04/07/2025 |
New York Yankees optioned LHP Brent Headrick to Scranton/Wilkes-Barre RailRiders. [Auto] |
| 04/07/2025 |
Scranton/Wilkes-Barre RailRiders activated LHP Brent Headrick. [Auto] |
| 04/23/2025 |
Scranton/Wilkes-Barre RailRiders placed LHP Brent Headrick on the 7-day injured list. [Auto] |
| 05/22/2025 |
New York Yankees recalled LHP Brent Headrick from Scranton/Wilkes-Barre RailRiders. [Auto] |
| 06/12/2025 |
New York Yankees optioned LHP Brent Headrick to Scranton/Wilkes-Barre RailRiders. [Auto] |
| 06/12/2025 |
Scranton/Wilkes-Barre RailRiders activated LHP Brent Headrick. [Auto] |
| 06/25/2025 |
Scranton/Wilkes-Barre RailRiders placed LHP Brent Headrick on the 7-day injured list. [Auto] |
| 07/19/2025 |
Scranton/Wilkes-Barre RailRiders activated LHP Brent Headrick from the 7-day injured list. [Auto] |
| 07/27/2025 |
New York Yankees recalled LHP Brent Headrick from Scranton/Wilkes-Barre RailRiders. [Auto] |
| 11/25/2025 |
Received a 1-year contract through automatic renewal worth a total of $740,000. |
| 01/01/2026 |
OSA scouting updated ratings (potential): Stuff: 65 (70); Movement: 45 (45); Control: 80 (80). |
| 11/28/2026 |
Received a 1-year contract through automatic renewal worth a total of $740,000. |
| 01/01/2027 |
OSA scouting updated ratings (potential): Stuff: 75 (80); Movement: 45 (45); Control: 80 (80). |
| 03/31/2027 |
Was claimed off waivers by Athletics while with New York. |
| 11/30/2027 |
Received a 1-year contract through automatic renewal worth a total of $740,000. |
| 01/01/2028 |
OSA scouting updated ratings (potential): Stuff: 80 (80); Movement: 45 (45); Control: 75 (75). |
| 05/15/2028 |
Injured on 05/12/2028, diagnosed with a strained hamstring, will miss 5 weeks. |
| 07/27/2028 |
Was traded by the Las Vegas Athletics to the Los Angeles Angels in exchange for C Hector Cruz and SP Oscar Rivera. |
| 11/07/2028 |
Signed a 1-year contract extension worth a total of $1,300,000 with the Los Angeles Angels organization. |
| 01/01/2029 |
OSA scouting updated ratings (potential): Stuff: 80 (80); Movement: 45 (45); Control: 75 (75). |
| 11/05/2029 |
Signed a 1-year contract extension worth a total of $2,800,000 with the Los Angeles Angels organization. |
| 01/01/2030 |
OSA scouting updated ratings (potential): Stuff: 80 (80); Movement: 50 (50); Control: 80 (80). |
| 02/13/2030 |
Injured (dehydration),day-to-day for 3 days. |
| 11/06/2030 |
Signed a 1-year contract extension worth a total of $4,520,000 with the Los Angeles Angels organization. |
| 01/01/2031 |
OSA scouting updated ratings (potential): Stuff: 80 (80); Movement: 50 (50); Control: 75 (75). |
| 02/18/2031 |
Signed a 2-year contract extension worth a total of $38,000,000 with the Los Angeles Angels organization. |
| 01/01/2032 |
OSA scouting updated ratings (potential): Stuff: 80 (80); Movement: 50 (50); Control: 80 (80). |
| 02/18/2032 |
Unsuccessfully completed training to improve his secondary pitch at the Los Angeles Angels development complex. |
| 09/06/2032 |
Injured (back stiffness),day-to-day for 1 day. |
| 01/01/2033 |
OSA scouting updated ratings (potential): Stuff: 80 (80); Movement: 50 (50); Control: 75 (75). |
| 09/01/2033 |
Injured (elbow inflammation),out for 4 weeks. |
| 10/08/2033 |
Signed a 2-year contract extension worth a total of $15,300,000 with the Los Angeles Angels organization. |
| 01/01/2034 |
OSA scouting updated ratings (potential): Stuff: 75 (75); Movement: 50 (50); Control: 75 (75). |
| 11/15/2034 |
Signed a 2-year contract extension worth a total of $15,800,000 with the Los Angeles Angels organization. |
| 01/01/2035 |
OSA scouting updated ratings (potential): Stuff: 75 (75); Movement: 50 (50); Control: 75 (75). |
| 06/07/2035 |
Injured (shoulder tendinitis),day-to-day for one week. |
| 07/02/2035 |
Suspended 3 games after ejection following a brawl. |
| 10/02/2035 |
Injured (cold),day-to-day for 1 day. |
| 10/03/2035 |
Injured (oblique strain),out for one week. |
| 10/14/2035 |
Wins the 2035 World Series with the Los Angeles Angels. |
| 01/01/2036 |
OSA scouting updated ratings (potential): Stuff: 70 (70); Movement: 50 (50); Control: 70 (70). |
| 05/02/2036 |
Injured (herniated disc (back)),out for one week. |