| Year | Broodmare | Sire—Dam | Damsire | Leading Earner, DOB, Sex, by Sire | Money Earned |
| 1990 | Whimsical Aire | Messenger of Song—Silky Steel | Steel Blade | Mahaska, 1987, m., by Just the Time | $235,253 |
| 1991 | Press to Test | Saltville—Rare Defense | Polynesian | Zama Hummer, 1988, m., by Knights Choice | $214,355 |
| 1992 | Sunrise River | Barbaric Spirit—What Next | *Tenerosa | Staff Rider, 1990, g., by Staff Writer | $364,699 |
| 1993 | Tea At Ten | Drone—Remuneration | Mississipian | Peterhof’s Patea, 1988, m., by Peterhof | $623,367 |
| 1994 | Highly Favored | Favorecidian—Minie Ball | Swoon’s Son | Favored One, 1992, m., by Son of Briartic | $227,965 |
| 1995 | Miss Stevenes | Lt. Stevens—Pywacket | Jester | Run Away Stevie, 1989, m., by Table Run | $468,267 |
| 1996 | Isle of View | Burd Alane—*Isle Lovagain | Combat | Comininalittlehot, 1991, g., by Just the Time | $393,627 |
| 1997 | Sendosha | Native Born—Seco’s Tanana | Windy Tide | Classy Rolls, 1991, m., by Rolls Aly | $75,306 |
| 1998 | Allazara | Empery—Apsara | Dancer’s Image | I. M. Bzy, 1995, g., by Kansas City | $261,802 |
| 1999 | Cocktail Talk | Princely Native—Stress Test | Quadrangle | Cocktails Anyone, 1993, m., by Petersburg | $242,545 |
| 2000 | Outofthebluebell | Red Ryder—Nachez Bluebell | Star Envoy | Rings a Chime, 1997, m., by Metfield | $606,315 |
| 2001 | Springhurst | Lord At War (Arg)—Del Dun Gee | Bold Dun-Cee | Tali’sluckybusride, 1999, m., by Delineator | $245,160 |
| 2002 | Kildare | Flying Paster—Tara’s Hall | Envoy | No Turbulence, 1999, m., by Skywalker | $200,855 |
| 2003 | Taj Aire | Taj Alriyadh—Whimsical Aire | Messenger of Song | Tropics, 2008, h., by Speightstown | $924,685 |
| 2004 | Crafty Court | Crafty Native—Morning Court | Prince o’ Morn | Court’s in Session, 1999, g., by Petersburg | $341,155 |
| 2005 | Takeaway | Fly So Free—Table Frolic | Never Tabled | Hail to the NIle, 2011, g., by Pioneerof the Nile | $257,721 |
| 2006 | Pure Wool | Relaunch—Sheepish Grin | Our Native | Pure as Gold, 2002, g., by Stolen Gold | $476,444 |
| 2007 | Nightatmisskittys | Al Mamoon—Skysweeper | Ack Ack | Dandy Dora, 2006, m., by Katowice | $127,910 |
| 2008 | Exploded’s Girl | Exploded—Western Starlet | Olympiad King | I’madrifter, 1998, h., by Slewdledo | $291,212 |
| 2009 | Irish Toast | Synastry—Bix’s Bet | Just the Time | Atta Boy Roy, 2005, h., by Tribunal | $602,276 |
| 2010 | Windsong Maria | Exclusive Bidder—Krugerrand Queen | Turn the Trick | Makors Mark, 1997, h., by Son of Briartic | $430,753 |
| 2011 | Peaceful Wings | Halo—Belle Gallante | *Gallant Man | Jebrica, 2008, g., by Liberty Gold | $342,253 |
| 2012 | Coup de Foudre | Basket Weave—Lorrains Love | Sauce Boat | Absolutely Cool, 2007, g., by Absolute Harmony | $406,892 |
| 2013 | Julia Rose | Basket Weave—Cure My Blue’s | Cure the Blues | Noosa Beach, 2006, g., by Harbor the Gold | $524,472 |
| 2014 | Striking Scholar | Smart Strike—Degree | Vanlandingham | Stryker Phd, 2009, g., by Bertrando | $631,011 |
| 2015 | Bahati | Horse Chestnut (SAf)—Drouth Willow | Premiership | Del Rio Harbor, 2011, g., by Harbor the Gold | $264,439 |
| 2016 | No Constraints | Katowice—Nightatmisskittys | Al Mamoon | Citizen Kitty, 2012, m., by Proud Citizen | $222,301 |
| 2017 | Chedoodle | Slewdledo—Chena | Chisos | Mike Man’s Gold, 2010, g., by Liberty Gold | $380,427 |
| 2018 | Premo Copy | Supremo—Soft Copy | Staff Writer | Baja Sur, 2016, g., by Smiling Tiger | $259,870 |
| 2019 | Trainingat the Bar | Valid Wager—Lady Lamar | Marquetry | Alittlelesstalk, 2016, m., by Demon Warlock | $170,226 |
| 2020 | Melba Jewel | Cahill Road—Chasseur Dame | French Legionaire | Elliott Bay, 2015, g., by Harbor the Gold | $194,927 |
| 2021 | Brookie Girl | Proud Citizen—Skatesheba (Fr) | Green Tune | Papa’s Golden Boy, 2016, g., by Harbor the Gold | $254,371 |
| 2022 | Holy Rose | Touch Gold—Holy Blitz | Holy Bull | Cats Touch, 2016, g., by Parker’s Storm Cat | $134,274 |
| 2023 | Moscow Symphony | Moscow Ballet—Margaret Booth | Well Decorated | Things Happen, 2002, g., by High Brite | $110,029 |
