| 01/02/1997 | Drafted in the 1997 inaugural draft (Round 10, Pick 15, 177th overall Pick) by the Chicago Grizzlies. |
| 09/14/1997 | Injured (back spasms), day-to-day for 2 weeks. |
| 11/09/1997 | Received a 1-year contract worth a total of $1,777,500 through arbitration. |
| 01/01/1998 | SISA scouting updated ratings (potential): Stuff: 5 (4); Movement: 8 (6); Control: 9 (7). |
| 11/10/1998 | Became a free agent. |
| 11/30/1998 | Signed a 1-year contract worth a total of $7,270,000 with the Chicago Grizzlies organization. |
| 01/01/1999 | SISA scouting updated ratings (potential): Stuff: 5 (4); Movement: 8 (6); Control: 9 (7). |
| 07/03/1999 | Signed a 1-year contract extension worth a total of $7,270,000 with the Chicago Grizzlies organization. |
| 01/01/2000 | SISA scouting updated ratings (potential): Stuff: 5 (4); Movement: 8 (6); Control: 9 (7). |
| 06/22/2000 | Was selected to the 2000 Over The Mound All-Star Game. |
| 09/08/2000 | Signed a 1-year contract extension worth a total of $7,270,000 with the Chicago Grizzlies organization. |
| 01/01/2001 | SISA scouting updated ratings (potential): Stuff: 5 (4); Movement: 8 (6); Control: 9 (7). |
| 06/21/2001 | Was selected to the 2001 Over The Mound All-Star Game. |
| 06/26/2001 | Signed a 1-year contract extension worth a total of $7,270,000 with the Chicago Grizzlies organization. |
| 01/01/2002 | SISA scouting updated ratings (potential): Stuff: 5 (4); Movement: 8 (6); Control: 9 (7). |
| 06/01/2002 | Wins the OTM WL Pitcher of the Month Award. |
| 06/20/2002 | Was selected to the 2002 Over The Mound All-Star Game. |
| 07/25/2002 | Signed a 1-year contract extension worth a total of $4,190,000 with the Chicago Grizzlies organization. |
| 01/01/2003 | SISA scouting updated ratings (potential): Stuff: 5 (4); Movement: 8 (6); Control: 9 (7). |
| 06/10/2003 | Signed a 1-year contract extension worth a total of $4,280,000 with the Chicago Grizzlies organization. |
| 06/26/2003 | Was selected to the 2003 Over The Mound All-Star Game. |
| 01/01/2004 | SISA scouting updated ratings (potential): Stuff: 4 (4); Movement: 8 (6); Control: 9 (7). |
| 03/26/2004 | Signed a 1-year contract extension worth a total of $4,280,000 with the Chicago Grizzlies organization. |
| 01/01/2005 | SISA scouting updated ratings (potential): Stuff: 4 (4); Movement: 8 (6); Control: 9 (7). |
| 03/25/2005 | Injured (strained back muscle), out for 6 weeks. |
| 10/13/2005 | Signed a 3-year contract extension worth a total of $13,080,000 with the Chicago Grizzlies organization. |
| 01/01/2006 | SISA scouting updated ratings (potential): Stuff: 4 (4); Movement: 8 (6); Control: 9 (7). |
| 01/01/2007 | SISA scouting updated ratings (potential): Stuff: 3 (4); Movement: 7 (6); Control: 9 (7). |
| 01/01/2008 | SISA scouting updated ratings (potential): Stuff: 3 (4); Movement: 7 (6); Control: 9 (7). |