| Player History |
| 05-10-2019 | Pitches a 5-hit shutout against the California Angels with 7 strikeouts and 0 BB allowed! |
| 05-16-2019 | Pitches a 4-hit shutout against the Minnesota Twins with 9 strikeouts and 0 BB allowed! |
| 06-29-2019 | Was selected to the 2019 Cooperstown Diamond Legends All-Star Game. |
| 07-01-2019 | Wins the CDL AL Pitcher of the Month Award. |
| 09-01-2019 | Wins the CDL AL Pitcher of the Month Award. |
| 11-16-2019 | Wins the 2019 CDL AL Cy Young Award. |
| 11-24-2019 | Received a 1-year contract worth a total of $300,000 through automatic renewal. |
| 01-01-2020 | SISA scouting updated ratings (potential): Stuff: 72 (70); Movement: 95 (92); Control: 101 (100). |
| 06-29-2020 | Was selected to the 2020 Cooperstown Diamond Legends All-Star Game. |
| 08-17-2020 | Pitches a PERFECT GAME against the Oakland Athletics, striking out 12 hitters! |
| 08-27-2020 | Pitches a 5-hit shutout against the Kansas City Royals with 8 strikeouts and 0 BB allowed! |
| 11-16-2020 | Received a 1-year contract worth a total of $300,000 through automatic renewal. |
| 01-01-2021 | SISA scouting updated ratings (potential): Stuff: 69 (70); Movement: 94 (92); Control: 99 (100). |
| 05-03-2021 | Signed a 2-year contract extension worth a total of $12,300,000 with the Boston Red Sox organization. |
| 06-29-2021 | Was selected to the 2021 Cooperstown Diamond Legends All-Star Game. |
| 08-01-2021 | Wins the CDL AL Pitcher of the Month Award. |
| 08-07-2021 | Pitches a 6-hit shutout against the Oakland Athletics with 10 strikeouts and 0 BB allowed! |
| 01-01-2022 | SISA scouting updated ratings (potential): Stuff: 69 (70); Movement: 93 (92); Control: 99 (100). |
| 04-04-2022 | Signed a 7-year contract extension worth a total of $94,960,000 with the Boston Red Sox organization. |
| 06-29-2022 | Was selected to the 2022 Cooperstown Diamond Legends All-Star Game. |
| 01-01-2023 | SISA scouting updated ratings (potential): Stuff: 66 (69); Movement: 93 (92); Control: 99 (100). |
| 04-29-2023 | Pitches a 1-hit shutout against the Oakland Athletics with 7 strikeouts and 0 BB allowed! |
| 09-08-2023 | Injured (strained bicep tendon), out for 4 weeks. |
| 01-01-2024 | SISA scouting updated ratings (potential): Stuff: 65 (67); Movement: 94 (92); Control: 100 (100). |
| 02-24-2024 | Was traded by the Boston Red Sox to the San Francisco Giants, along with SP J. Lapinski, 3B M. Moses, in exchange for LF D. Stubbs, 3B K. Kouzmanoff, 2B T. Nilsson, a 1st draft pick, a 2nd draft pick, a 3rd draft pick. |
| 05-14-2024 | Pitches a 1-hit shutout against the Los Angeles Dodgers with 9 strikeouts and 0 BB allowed! |
| 06-20-2024 | Was selected to the 2024 Cooperstown Diamond Legends All-Star Game. |
| 07-01-2024 | Wins the CDL NL Pitcher of the Month Award. |
| 08-07-2024 | Pitches a 5-hit shutout against the Cincinnati Reds with 8 strikeouts and 0 BB allowed! |
| 09-01-2024 | Wins the CDL NL Pitcher of the Month Award. |
| 10-07-2024 | Pitches a 3-hit shutout against the Chicago (N) Cubs with 10 strikeouts and 0 BB allowed! |
| 10-23-2024 | Won the 2024 Cooperstown Diamond Legends CDL World Series with the San Francisco Giants! |
| 11-05-2024 | Wins the 2024 CDL NL Cy Young Award. |
| 01-01-2025 | SISA scouting updated ratings (potential): Stuff: 65 (67); Movement: 93 (92); Control: 101 (100). |
| 04-01-2025 | Pitches a 3-hit shutout against the San Diego Padres with 11 strikeouts and 0 BB allowed! |
| 04-27-2025 | Pitches a 6-hit shutout against the Cincinnati Reds with 7 strikeouts and 0 BB allowed! |
| 05-01-2025 | Wins the CDL NL Pitcher of the Month Award. |
| 06-20-2025 | Was selected to the 2025 Cooperstown Diamond Legends All-Star Game. |
| 07-25-2025 | Injured (back spasms), out for 1-2 weeks. |
| 08-16-2025 | Injured (strained back muscle), out for 1-2 weeks. |
| 09-19-2025 | Pitches a 4-hit shutout against the San Diego Padres with 8 strikeouts and 0 BB allowed! |
| 11-02-2025 | Wins the 2025 CDL NL Cy Young Award. |
| 01-01-2026 | SISA scouting updated ratings (potential): Stuff: 67 (67); Movement: 94 (92); Control: 99 (100). |
| 04-01-2026 | Earns his 200th career Cooperstown Diamond Legends victory! |
| 05-01-2026 | Wins the CDL NL Pitcher of the Month Award. |
| 06-01-2026 | Wins the CDL NL Pitcher of the Month Award. |
| 06-20-2026 | Was selected to the 2026 Cooperstown Diamond Legends All-Star Game. |
| 11-01-2026 | Wins the 2026 CDL NL Cy Young Award. |
| 01-01-2027 | SISA scouting updated ratings (potential): Stuff: 66 (67); Movement: 93 (92); Control: 99 (100). |
| 05-18-2027 | Pitches a 2-hit shutout against the Philadelphia Phillies with 9 strikeouts and 0 BB allowed! |
| 06-01-2027 | Wins the CDL NL Pitcher of the Month Award. |
| 06-20-2027 | Was selected to the 2027 Cooperstown Diamond Legends All-Star Game. |
| 07-01-2027 | Wins the CDL NL Pitcher of the Month Award. |
| 08-01-2027 | Wins the CDL NL Pitcher of the Month Award. |
| 09-10-2027 | Earns his 250th career Cooperstown Diamond Legends victory! |
| 11-03-2027 | Wins the 2027 CDL NL Cy Young Award. |
| 12-19-2027 | Was traded by the San Francisco Giants to the Cleveland Indians in exchange for LF H. Denton, SP D. Haynes, SP R. Flores, a 3rd draft pick. |
| 01-01-2028 | OSA scouting updated ratings (potential): Stuff: 47 (66); Movement: 88 (92); Control: 100 (100). |
| 05-27-2028 | Pitches a 3-hit shutout against the Detroit Tigers with 3 strikeouts and 0 BB allowed! |
| 06-01-2028 | Wins the CDL AL Pitcher of the Month Award. |
| 06-20-2028 | Was selected to the 2028 Cooperstown Diamond Legends All-Star Game. |
| 07-29-2028 | Pitches a 3-hit shutout against the Minnesota Twins with 7 strikeouts and 0 BB allowed! |
| 08-11-2028 | Collects his 3000th career Cooperstown Diamond Legends strikeout! |
| 08-29-2028 | Pitches a 2-hit shutout against the Baltimore Orioles with 13 strikeouts and 0 BB allowed! |
| 09-01-2028 | Wins the CDL AL Pitcher of the Month Award. |
| 11-02-2028 | Wins the 2028 CDL AL Cy Young Award. |
| 01-01-2029 | OSA scouting updated ratings (potential): Stuff: 41 (66); Movement: 88 (92); Control: 100 (100). |
| 05-01-2029 | Wins the CDL AL Pitcher of the Month Award. |
| 06-20-2029 | Was selected to the 2029 Cooperstown Diamond Legends All-Star Game. |
| 01-01-2030 | OSA scouting updated ratings (potential): Stuff: 37 (66); Movement: 80 (92); Control: 100 (100). |
| 04-12-2030 | Pitches a 3-hit shutout against the New York (A) Yankees with 4 strikeouts and 1 BB allowed! |
| 04-19-2030 | Earns his 300th career Cooperstown Diamond Legends victory! |
| 06-01-2030 | Pitches a 6-hit shutout against the Toronto Blue Jays with 3 strikeouts and 0 BB allowed! |
| 06-20-2030 | Was selected to the 2030 Cooperstown Diamond Legends All-Star Game. |
| 07-18-2030 | Signed a 2-year contract extension worth a total of $31,320,000 with the Cleveland Indians organization. |
| 08-20-2030 | Suspended 7 games after ejection following a brawl. |