| Player History |
| 03-31-1998 | Named the #10 prospect in the MLB |
| 05-24-1998 | Pitches a 4-hit shutout against the Newark Fever with 9 strikeouts and 0 BB allowed! |
| 05-31-1998 | Was selected to the 1998 ML Double A All-Star Game. |
| 01-01-1999 | OSA scouting updated ratings (potential): Stuff: 81 (77); Movement: 78 (95); Control: 64 (95). |
| 04-04-1999 | Named the #33 prospect in the MLB |
| 06-04-1999 | Was selected to the 1999 Pacific Coast League All-Star Game. |
| 07-01-1999 | Was traded by the Houston Astros to the Boston Red Sox, along with CL B. Kim, $4,000,000, in exchange for SS N. Garciaparra, a 2nd draft pick. |
| 07-01-1999 | Released by the Boston organization. |
| 01-01-2000 | OSA scouting updated ratings (potential): Stuff: 81 (77); Movement: 89 (95); Control: 80 (95). |
| 03-29-2000 | Named the #29 prospect in the MLB |
| 06-12-2000 | Pitches a 5-hit shutout against the New York (A) Yankees with 10 strikeouts and 0 BB allowed! |
| 07-30-2000 | Injured (strained bicep tendon), day-to-day for 2 weeks. |
| 11-20-2000 | Received a 1-year contract worth a total of $263,807 through automatic renewal. |
| 01-01-2001 | OSA scouting updated ratings (potential): Stuff: 80 (88); Movement: 90 (95); Control: 83 (95). |
| 04-19-2001 | Pitches a 3-hit shutout against the Tampa Bay Devil Rays with 6 strikeouts and 0 BB allowed! |
| 06-01-2001 | Wins the MLB AL Pitcher of the Month Award. |
| 07-08-2001 | Was selected to the 2001 Major League Baseball All-Star Game. |
| 09-25-2001 | Pitches a 6-hit shutout against the Baltimore Orioles with 12 strikeouts and 1 BB allowed! |
| 09-30-2001 | Pitches a 3-hit shutout against the Detroit Tigers with 8 strikeouts and 0 BB allowed! |
| 10-27-2001 | Wins the 2001 MLB AL Cy Young Award. |
| 11-19-2001 | Received a 1-year contract worth a total of $263,807 through automatic renewal. |
| 01-01-2002 | OSA scouting updated ratings (potential): Stuff: 91 (88); Movement: 95 (95); Control: 97 (95). |
| 04-29-2002 | Injured (back spasms), out for 1-2 weeks. |
| 06-25-2002 | Pitches a 1-hit shutout against the Tampa Bay Devil Rays with 8 strikeouts and 1 BB allowed! |
| 07-06-2002 | Was selected to the 2002 Major League Baseball All-Star Game. |
| 07-30-2002 | Pitches a 3-hit shutout against the Baltimore Orioles with 7 strikeouts and 2 BB allowed! |
| 08-01-2002 | Wins the MLB AL Pitcher of the Month Award. |
| 09-07-2002 | Pitches a 2-hit shutout against the Oakland Athletics with 11 strikeouts and 1 BB allowed! |
| 09-25-2002 | Pitches a 2-hit shutout against the Toronto Blue Jays with 7 strikeouts and 1 BB allowed! |
| 10-29-2002 | Won the 2002 Major League Baseball World Series with the Boston Red Sox! |
| 10-30-2002 | Wins the 2002 MLB AL Cy Young Award. |
| 11-19-2002 | Received a 1-year contract worth a total of $4,293,000 through arbitration. |
| 01-01-2003 | OSA scouting updated ratings (potential): Stuff: 94 (91); Movement: 95 (93); Control: 92 (93). |
| 05-15-2003 | Pitches a 3-hit shutout against the Texas Rangers with 6 strikeouts and 1 BB allowed! |
| 07-01-2003 | Wins the MLB AL Pitcher of the Month Award. |
| 07-07-2003 | Was selected to the 2003 Major League Baseball All-Star Game. |
| 09-01-2003 | Wins the MLB AL Pitcher of the Month Award. |
| 09-08-2003 | Pitches a 3-hit shutout against the Baltimore Orioles with 6 strikeouts and 1 BB allowed! |
| 09-21-2003 | Pitches a 2-hit shutout against the Cleveland Indians with 7 strikeouts and 2 BB allowed! |
| 10-28-2003 | Wins the 2003 MLB AL Cy Young Award. |
| 11-17-2003 | Received a 1-year contract worth a total of $4,013,800 through arbitration. |
| 01-01-2004 | OSA scouting updated ratings (potential): Stuff: 92 (91); Movement: 92 (93); Control: 93 (93). |
| 06-12-2004 | Signed a 7-year contract extension worth a total of $60,460,000 with the Boston Red Sox organization. |
| 07-01-2004 | Wins the MLB AL Pitcher of the Month Award. |
| 07-09-2004 | Pitches a 3-hit shutout against the Texas Rangers with 8 strikeouts and 1 BB allowed! |
| 07-11-2004 | Was selected to the 2004 Major League Baseball All-Star Game. |
| 10-29-2004 | Wins the 2004 MLB AL Cy Young Award. |
| 01-01-2005 | OSA scouting updated ratings (potential): Stuff: 93 (91); Movement: 91 (93); Control: 92 (93). |
| 10-31-2005 | Won the 2005 Major League Baseball World Series with the Boston Red Sox! |
| 01-01-2006 | OSA scouting updated ratings (potential): Stuff: 94 (91); Movement: 92 (93); Control: 95 (93). |
| 06-09-2006 | Pitches a 4-hit shutout against the Texas Rangers with 10 strikeouts and 0 BB allowed! |
| 07-01-2006 | Wins the MLB AL Pitcher of the Month Award. |
| 07-09-2006 | Was selected to the 2006 Major League Baseball All-Star Game. |
| 08-01-2006 | Wins the MLB AL Pitcher of the Month Award. |
| 01-01-2007 | OSA scouting updated ratings (potential): Stuff: 92 (91); Movement: 92 (93); Control: 93 (93). |
| 05-01-2007 | Wins the MLB AL Pitcher of the Month Award. |
| 07-07-2007 | Was selected to the 2007 Major League Baseball All-Star Game. |
| 08-04-2007 | Pitches a 5-hit shutout against the Seattle Mariners with 7 strikeouts and 1 BB allowed! |
| 09-11-2007 | Pitches a 2-hit shutout against the Tampa Bay Devil Rays with 10 strikeouts and 0 BB allowed! |
| 10-11-2007 | Pitches a 4-hit shutout against the Toronto Blue Jays with 5 strikeouts and 1 BB allowed! |
| 11-08-2007 | Won the 2007 Major League Baseball World Series with the Boston Red Sox! |
| 01-01-2008 | OSA scouting updated ratings (potential): Stuff: 90 (91); Movement: 90 (93); Control: 95 (93). |