Past Winners of the Woodbine Mile
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| 2009 |
Ventura (jockey Garrett Gomez, trainer Robert Frankel, owner Juddmonte Farms Inc.); paid $6.20; defeated Ferneley by one length; first filly or mare winner; established new stakes record 1:32.04 |
| 2008 |
Rahy's Attorney (jockey Slade Callaghan, trainer Ian Black, owners Ellie Boje Farms, Jim and Jean MacLellan, Mitch Peters and Dean Read); paid $27.30 to win; beat Ventura by one and a quarter length
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| 2007 |
Shakespeare (jockey Garrett Gomez, trainer Kiaran McLaughlin, owners William Schettine and Dell Ridge Farm); paid $5.90 to win; beat Kip Deville by one length
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| 2006 |
Becrux (jockey Patrick Valenzuela, trainer Neil Drysdale, owners Team Valor and Gary Barber); paid $18.70 to win; beat Rebel Rebel by a neck
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| 2005 |
Leroidesanimaux (jockey John Velazquez, trainer Robert Frankel, owner TNT Stud); paid $3.30 to win; beat Mobil by seven and three-quarter lengths
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| 2004 |
Soaring Free (jockey Todd Kabel, trainer Mark Frostad, owner-breeder Sam-Son Farm); paid $6.30 to win; beat Perfect Soul by three-quarters of a length
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| 2003 |
Touch of the Blues (jockey Kent Desormeaux, trainer Neil Drysdale, owner Gainsborough Farm LLC, breeder Gainsborough Stud); paid $12.90 to win; beat Soaring Free by one-half length
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| 2002 |
Good Journey (jockey Pat Day, trainer Wally Dollase, owner Flaxman Holdings Ltd., Gary Margolis, Michael Jarvis & Partners, breeder Flaxman Holdings Ltd.); paid $8.40 to win; beat Chopinina by one length
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| 2001 |
Numerous Times (jockey Patrick Husbands, trainer Sid Attard, owner The Committee Stable, breeder Patrick Ballentine Estate); paid $15.40 to win; beat Affirmed Success by a nose
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| 2000 |
Riviera (jockey John Velazquez, trainer Robert Frankel, owner Edmund Gann, breeder Janus Bloodstock Inc.); paid $23.10 to win; beat Arkadian Hero by a nose
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| 1999 |
Quiet Resolve (jockey Robert Landry, trainer Mark Frostad, owner-breeder Sam-Son Farm); paid $91.10 to win; crossed the wire second but placed first after Hawksley Hill was disqualified for interference in the stretch
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| 1998 |
Labeeb (jockey Kent Desormeaux, trainer Neil Drysdale, owner Gainsborough Farm LLC, breeder Brick Kiln Stud & Lariston Apartments Ltd.); paid $6.60 to win; beat Jim and Tonic by a head
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| 1997 |
Geri (jockey Chris Antley, trainer Bill Mott, owner-breeder Allen Paulson); paid $18.90 to win; beat Helmsman by one and one-half lengths
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