| Cy Young Awards | ||
| Season | Player (Team) | Points |
| 2008 #19 | John Lackey (HTX) | 132 |
| 2007 #18 | B.J. Ryan (DOT) | 119 |
| 2007 #17 | Dan Haren (CHK) | 113 |
| 2006 #16 | Chris Carpenter (DEM) | 117 |
| 2006 #15 | Derrick Turnbow (HTX) | 112 |
| 2005 #14 | Carlos Zambrano (DOT) | 115 |
| 2005 #13 | Johan Santana (FHJ) | 125 |
| 2004 #12 | Gaylord Perry (DEM) | 136 |
| 2004 #11 | Kerry Wood (CHK) | 118 |
| 2003 #10 | Randy Johnson (WSD) | 124 |
| 2003 #9 | Derek Lowe (WJG) | 117 |
| 2002 #8 | Chan Ho Park (NBD) | 117 |
| 2002 #7 | Chan Ho Park (NBD) | 127 |
| 2001 #6 | Pedro Martinez (WSD) | 117 |
| 2001 #5 | Pedro Martinez (WSD) | 116 |
| 2000 #4 | Kevin Millwood (WFY) | 108 |
| 2000 #3 | Randy Johnson (WSD) | 107 |
| 1999 #2 | Roger Clemens (TPH) | 111 |
| 1999 #1 | Randy Johnson (SMA) | 114 |
| M.V.P. Awards | ||
| Season | Player (Team) | Points |
| 2008 #19 | John Lackey (HTX) | 424 |
| 2007 #18 | Albert Pujols (CHK) | 410 |
| 2007 #17 | David Ortiz (DOT) | 378 |
| 2006 #16 | Alex Rodriguez (HTX) | 370 |
| 2006 #15 | Derrek Lee (WFY) | 382 |
| 2005 #14 | Lance Berkman (DEM) | 374 |
| 2005 #13 | Johan Santana (FHJ) | 400 |
| 2004 #12 | Albert Pujols (FVD) | 392 |
| 2004 #11 | Alex Rodriguez (HTX) | 391 |
| 2003 #10 | Alex Rodriguez (HTX) | 397 |
| 2003 #9 | Alex Rodriguez (HTX) | 413 |
| 2002 #8 | Barry Bonds (FUS) | 394 |
| 2002 #7 | Barry Bonds (FUS) | 370 |
| 2001 #6 | Todd Helton (FUS) | 375 |
| 2001 #5 | Todd Helton (FUS) | 375 |
| 2000 #4 | Derek Jeter (UTC) | 369 |
| 2000 #3 | Mark McGwire (MOP) | 398 |
| 1999 #2 | Juan Gonzalez (MOP) | 373 |
| 1999 #1 | Alex Rodriguez (HTX) | 385 |
| Manager of the Year Awards | ||
| Season | Manager (Team) | Rank |
| 2008 #19 | Trey M. (BRS) | 1st |
| 2007 #18 | Jonathan P. (DEM) | 1st |
| 2007 #17 | Mike E. (CHK) | 5th |
| 2006 #16 | Mike E. (CHK) | 3rd |
| 2006 #15 | Darren B. (HTX) | 1st |
| 2005 #14 | Frank C. (DOT) | 2nd |
| 2005 #13 | Dan S. (FVD) | 6th |
| 2004 #12 | Jonathan P. (DEM) | 5th |
| 2004 #11 | Mike E. (CHK) | 2nd |
| 2003 #10 | Shane W. (WJG) | 1st |
| 2003 #9 | Josh P. (WSD) | 3rd |
| 2002 #8 | Mike E. (CHK) | 5th |
| 2002 #7 | Mike E. (CHK) | 5th |
| 2001 #6 | Josh P. (WSD) | 5th |
| 2001 #5 | Darren B. (HTX) | 1st |
| 2000 #4 | Darren B. (HTX) | 5th |
| 2000 #3 | Darren B. (HTX) | 1st |
| 1999 #2 | Rob S. (MOP) | 4th |
| 1999 #1 | Steve G. (MSB) | 3rd |