| Player History |
| 01-01-2010 | Drafted in the 2010 inaugural draft (Round 7, Pick 2, 182nd overall Pick) by the Chicago Cubs. |
| 11-17-2010 | Received a 1-year contract worth a total of $2,355,200 through arbitration. |
| 01-01-2011 | SISA scouting updated ratings (potential): Stuff: 11 (11); Movement: 17 (17); Control: 12 (12). |
| 06-27-2011 | Was selected to the 2011 Major League Baseball All-Star Game. |
| 11-20-2011 | Received a 1-year contract worth a total of $2,860,900 through arbitration. |
| 01-01-2012 | SISA scouting updated ratings (potential): Stuff: 8 (8); Movement: 14 (14); Control: 15 (15). |
| 11-16-2012 | Received a 1-year contract worth a total of $3,087,000 through arbitration. |
| 01-01-2013 | SISA scouting updated ratings (potential): Stuff: 8 (8); Movement: 15 (15); Control: 16 (16). |
| 09-13-2013 | Signed a 4-year contract extension worth a total of $17,040,000 with the Chicago Cubs organization. |
| 01-01-2014 | SISA scouting updated ratings (potential): Stuff: 6 (7); Movement: 14 (14); Control: 14 (14). |
| 01-01-2015 | SISA scouting updated ratings (potential): Stuff: 5 (6); Movement: 16 (16); Control: 13 (13). |
| 01-01-2016 | SISA scouting updated ratings (potential): Stuff: 6 (6); Movement: 13 (13); Control: 14 (14). |
| 08-28-2016 | Pitches a 5-hit shutout against the Cincinnati Reds with 6 strikeouts and 2 BB allowed! |
| 09-01-2016 | Wins the MLB NL Pitcher of the Month Award. |
| 01-01-2017 | SISA scouting updated ratings (potential): Stuff: 7 (7); Movement: 15 (15); Control: 12 (12). |
| 03-29-2017 | Signed a 1-year contract extension worth a total of $1,290,000 with the Chicago Cubs organization. |
| 01-01-2018 | SISA scouting updated ratings (potential): Stuff: 8 (8); Movement: 15 (15); Control: 14 (14). |
| 05-22-2018 | Signed a 1-year contract extension worth a total of $1,290,000 with the Chicago Cubs organization. |
| 08-28-2018 | Injured (tender shoulder), out for 2 weeks. |
| 01-01-2019 | SISA scouting updated ratings (potential): Stuff: 6 (6); Movement: 15 (15); Control: 14 (14). |
| 03-15-2019 | Signed a 1-year contract extension worth a total of $1,290,000 with the Chicago Cubs organization. |
| 08-17-2019 | Injured (back spasms), out for 2 weeks. |
| 01-01-2020 | SISA scouting updated ratings (potential): Stuff: 6 (6); Movement: 14 (14); Control: 15 (15). |
| 06-29-2020 | Signed a 1-year contract extension worth a total of $1,290,000 with the Chicago Cubs organization. |
| 01-01-2021 | SISA scouting updated ratings (potential): Stuff: 5 (6); Movement: 13 (14); Control: 13 (13). |
| 04-03-2021 | Signed a 1-year contract extension worth a total of $580,000 with the Chicago Cubs organization. |
| 12-26-2021 | Got claimed off waivers by New York while with Chicago. |
| 01-01-2022 | SISA scouting updated ratings (potential): Stuff: 4 (6); Movement: 11 (13); Control: 13 (13). |
| 03-14-2022 | Signed a 1-year contract extension worth a total of $580,000 with the New York Yankees organization. |
