| Year | Leading Sire | Sire | Dam, by Damsire |
| 1990 | Staff Writer | Northern Dancer | Twill, by Swaps |
| 1991 | Knights Choice | Drum Fire | Yang, by *Turn-to |
| 1992 | Staff Writer | Northern Dancer | Twill, by Swaps |
| 1993 | Son of Briartic | Briartic | Tabola, by Round Table |
| 1994 | Son of Briartic | Briartic | Tabola, by Round Table |
| 1995 | Son of Briartic | Briartic | Tabola, by Round Table |
| 1996 | Son of Briartic | Briartic | Tabola, by Round Table |
| 1997 | Son of Briartic | Briartic | Tabola, by Round Table |
| 1998 | Son of Briartic | Briarctic | Tabola, by Round Table |
| 1999 | Son of Briartic | Briartic | Tabola, by Round Table |
| 2000 | Cahill Road | Fappiano | Gana Facil, by *Le Fabuleux |
| 2001 | Son of Briartic | Briartic | Tabola, by Round Table |
| 2002* | Defensive Play | Fappiano | Safe Play, by Sham |
| 2002* | Slewdledo | Seattle Slew | M’lle. Cyanne, by Cyane |
| 2003 | Slewdledo | Seattle Slew | M’lle. Cyanne, by Cyane |
| 2004 | Slewdledo | Seattle Slew | M’lle. Cyanne, by Cyane |
| 2005 | Slewdledo | Seattle Slew | M’lle. Cyanne, by Cyane |
| 2006 | You and I | Kris S. | La Chaposa (Per), by Ups |
| 2007 | Matty G | Capote | Star Gem, by Pia Star |
| 2008 | Matty G | Capote | Star Gem, by Pia Star |
| 2009 | Matty G | Capote | Star Gem, by Pia Star |
| 2010 | Matty G | Capote | Star Gem, by Pia Star |
| 2011 | Parker’s Storm Cat | Storm Cat | Macoumba, by Mr. Prospector |
| 2012 | Parker’s Storm Cat | Storm Cat | Macoumba, by Mr. Prospector |
| 2013 | Parker’s Storm Cat | Storm Cat | Macoumba, by Mr. Prospector |
| 2014 | Parker’s Storm Cat | Storm Cat | Macoumba, by Mr. Prospector |
| 2015 | Parker’s Storm Cat | Storm Cat | Macoumba, by Mr. Prospector |
| 2016 | Parker’s Storm Cat | Storm Cat | Macoumba, by Mr. Prospector |
| 2017 | Parker’s Storm Cat | Storm Cat | Macoumba, by Mr. Prospector |
| 2018 | Atta Boy Roy | Tribunal | Irish Toast, by Synastry |
| 2019 | Atta Boy Roy | Tribunal | Irish Toast, by Synastry |
| 2020 | Atta Boy Roy | Tribunal | Irish Toast, by Synastry |
| 2021 | Conveyance | Indian Charlie | Emptythetill, by Holy Bull |
| 2022 | Conveyance | Indian Charlie | Emptythetill, by Holy Bull |
| 2023 | Conveyance | Indian Charlie | Emptythetill, by Holy Bull |
*Co-leading sires
