| Year | Leading Sire of 2YOs | Sire | Dam, by Damsire |
| 1990 | Knights Choice | Drum Fire | Yang, by *Turn-to |
| 1991 | Son of Briartic | Briartic | Tabola, by Round Table |
| 1992 | Staff Writer | Northern Dancer | Twill, by Swaps |
| 1993 | Knights Choice | Drum Fire | Yang, by *Turn-to |
| 1994 | Son of Briartic | Briartic | Tabola, by Round Table |
| 1995 | Tough Knight | Knights Choice | Countess Courage, by Captain Courageous |
| 1996 | Jazzing Around | Stop the Music | Fantastic Miss, by Jacinto |
| 1997 | Son of Briartic | Briartic | Tabola, by Round Table |
| 1998 | Demons Begone | Elocutionist | Roudy Angel, by Halo |
| 1999 | Son of Briartic | Briartic | Tabola, by Round Table |
| 2000 | Slewdledo | Seattle Slew | M’lle. Cyanne, by Cyane |
| 2001 | Delineator | Storm Cat | Mountain Climber, by *Grey Dawn II |
| 2002 | Slewdledo | Seattle Slew | M’lle. Cyanne, by Cyane |
| 2002 | |||
| 2003 | Slewdledo | Seattle Slew | M’lle. Cyanne, by Cyane |
| 2004 | Basket Weave | Best Turn | Pass the Basket, by Buckpasser |
| 2005 | Free At Last | Wild Again | Miss Blanche, by Faraway Son |
| 2006 | Free At Last | Wild Again | Miss Blanche, by Faraway Son |
| 2007 | Matty G | Capote | Star Gem, by Pia Star |
| 2008 | He’s Tops | Seattle Slew | She’s a Talent, by Mr. Prospector |
| 2009 | Tribunal | Deputy Minister | Six Crowns, by Secretariat |
| 2010 | Matty G | Capote | Star Gem, by Pia Star |
| 2011 | Cahill Road | Fappiano | Gana Facil, by *Le Fabuleux |
| 2012 | Matty G | Capote | Star Gem, by Pia Star |
| 2013 | Matty G | Capote | Star Gem, by Pia Star |
| 2014 | Private Gold | Seeking the Gold | Temper the Wind, by Elocutionist |
| 2015 | Abraaj | Carson City | Kris’s Intention, by Kris S. |
| 2016 | Coast Guard | Stormy Atlantic | Vassar, by Royal Academy |
| 2017 | Atta Boy Roy | Tribunal | Irish Toast, by Synastry |
| 2018 | He’s Tops | Seattle Slew | She’s a Talent, by Mr. Prospector |
| 2019 | Abraaj | Carson City | Kris’s Intention, by Kris S. |
| 2020 | Atta Boy Roy | Tribunal | Irish Toast, by Synastry |
| 2021 | Coast Guard | Stormy Atlantic | Vassar, by Royal Academy |
| 2022 | Coast Guard | Stormy Atlantic | Vassar, by Royal Academy |
| 2023 | Coast Guard | Stormy Atlantic | Vassar, by Royal Academy |
