| Player History |
| 01-01-2010 | Drafted in the 2010 inaugural draft (Round 10, Pick 1, 271st overall Pick) by the New York Yankees. |
| 11-17-2010 | Received a 1-year contract worth a total of $2,758,400 through arbitration. |
| 01-01-2011 | SISA scouting updated ratings (potential): Stuff: 20 (20); Movement: 16 (16); Control: 12 (12). |
| 11-20-2011 | Received a 1-year contract worth a total of $3,216,000 through arbitration. |
| 01-01-2012 | SISA scouting updated ratings (potential): Stuff: 17 (17); Movement: 16 (16); Control: 9 (9). |
| 05-28-2012 | Injured (dead arm syndrome), out for 2 weeks. |
| 08-23-2012 | Injured (hyperextended elbow), out for 5-6 weeks. |
| 11-16-2012 | Received a 1-year contract worth a total of $3,451,000 through arbitration. |
| 11-30-2012 | Was traded by the New York Yankees to the Pittsburgh Pirates in exchange for SP D. Rew, SS G. Brown. |
| 01-01-2013 | SISA scouting updated ratings (potential): Stuff: 18 (18); Movement: 14 (14); Control: 10 (10). |
| 11-21-2013 | Became a free agent. |
| 12-23-2013 | Signed a 2-year contract worth a total of $6,180,000 with the Pittsburgh Pirates organization. |
| 01-01-2014 | SISA scouting updated ratings (potential): Stuff: 18 (18); Movement: 15 (15); Control: 10 (10). |
| 06-27-2014 | Injured (tender elbow), day-to-day for 1-2 weeks. |
| 01-01-2015 | SISA scouting updated ratings (potential): Stuff: 18 (18); Movement: 14 (14); Control: 14 (14). |
| 11-22-2015 | Became a free agent. |
| 12-27-2015 | Signed a 2-year contract worth a total of $10,760,000 with the New York Yankees organization. |
| 01-01-2016 | SISA scouting updated ratings (potential): Stuff: 17 (17); Movement: 15 (15); Control: 10 (10). |
| 01-01-2017 | SISA scouting updated ratings (potential): Stuff: 18 (18); Movement: 13 (13); Control: 11 (11). |
| 06-18-2017 | Injured (strained bicep tendon), out for 2-3 weeks. |
| 09-01-2017 | Signed a 2-year contract extension worth a total of $11,360,000 with the New York Yankees organization. |
| 01-01-2018 | SISA scouting updated ratings (potential): Stuff: 17 (17); Movement: 14 (14); Control: 10 (11). |
| 03-13-2018 | Injured (finger blister), day-to-day for 1-2 weeks. |
| 04-08-2018 | Injured (strained bicep tendon), day-to-day for 2 weeks. |
| 07-07-2018 | Was selected to the 2018 Major League Baseball All-Star Game. |
| 09-01-2018 | Wins the MLB AL Pitcher of the Month Award. |
| 09-13-2018 | Pitches a 3-hit shutout against the Baltimore Orioles with 14 strikeouts and 0 BB allowed! |
| 11-06-2018 | Wins the 2018 MLB AL Cy Young Award. |
| 12-19-2018 | Signed a 4-year contract extension worth a total of $53,960,000 with the New York Yankees organization. |
| 01-01-2019 | SISA scouting updated ratings (potential): Stuff: 17 (18); Movement: 13 (13); Control: 10 (10). |
| 04-28-2019 | Injured (torn bicep muscle), out for 2 months. |
| 08-06-2019 | Pitches a 1-hit shutout against the Los Angeles Angels with 9 strikeouts and 1 BB allowed! |