Led by defending winner Notable Speech and standout U.S. horse Deterministic, Saturday’s $1 million Woodbine Mile promises to be an outstanding race. First run in 1988, the Woodbine Mile is one of the premier events for turf horses in North America. It was not always run on the grass, however. The first nine editions of the race were run on what was then a dirt main track at Woodbine and originally known as the Molson Export Challenge and then the Molson Export Million. The race did not move to a flat mile on the turf until the 1997 edition.

As both the Woodbine Mile and the Molson Million, the marquee Canadian event has always been both a prestigious prize in its own right, as well as an important prep leading to the Breeders’ Cup. From the inaugural edition won by Ballindaggin through Notable Speech in 2025, the race has consistently produced quality fields with noteworthy winners.

Counting down from five, let’s look back at the greatest winners from the excellent history of the race as both the Molson Million and the Woodbine Mile. My criteria for ranking the top five was based simply on which horses I believed to be the overall best during their racing career, with their performance in the race only considered when breaking ties. This list is sure to cause some serious discussion considering the number of greats that could not crack the top five, including Canadian Triple Crown winners, Breeders’ Cup winners, and Eclipse Award winners.

5. Prized (1989). Perhaps a forgotten name in the history of modern racing, the son of Kris S. was a uniquely talented runner for trainer Neil Drysdale. A contemporary of Sunday Silence and Easy Goer, Prized was an important contributor to the great year of racing that was 1989. A bit of a late developer, the Florida-bred burst on to the national scene by defeating heavily-favored Sunday Silence in the Swaps Stakes in July. He followed up that upset by traveling to Woodbine to win the then 1 ¼-mile Molson Export Million. Beaten in the Jockey Club Gold by Easy Goer, he then rewarded his connections' faith by winning the Breeders’ Cup Turf over a top international field in his first career race on grass. His career as an older horse was slowed by injuries, but he was still able to win a few graded stakes at Santa Anita Park in limited attempts. A winner of 9 of 17 races in his career, Prized makes this list for the magnitude of his victories as a 3-year-old.

4. Tepin (2016). The first of two females to crack this list, the daughter of Bernstein was one of the great American middle-distance turf runners of the 21^st century. Trained by Mark Casse, she was a graded stakes winner on the dirt at 2, but her racing career didn’t really get going until her 4-year-old season. Improving with each start, Tepin won her third Grade 1 race of that season with a decisive score in the Breeders’ Cup Mile at Keeneland. It was enough for a season-ending Eclipse Award as top turf female of 2015. She would win that award again with an even better season at 5. Her popular victory in the 2016 Woodbine Mile followed a Group 1 win at Royal Ascot and was her eighth consecutive graded stakes score. After finishing second in her final two career starts, including the Breeders’ Cup Mile at Santa Anita, Tepin retired with 13 wins in 23 career starts. She was inducted into the Hall of Fame in 2022.

Michael Burns/Woodbine

3. Dance Smartly (1991). One of Canada’s most beloved runners, the daughter of Danzig was an instant success in her native land. A stakes winner at Woodbine at 2, she traveled south for the first time to run third in the Breeders’ Cup Juvenile Fillies at Belmont Park. At 3, she proved unbeatable. Dance Smartly won all eight starts in 1991, including each leg of the Canadian Triple Crown, becoming only the second filly to sweep the series. Dance Smartly finished off her magical season with convincing wins in the Molson Million followed by the Breeders’ Cup Distaff at Churchill Downs. In the latter, she became the first Canadian-bred to win a Breeders’ Cup race. Dance Smartly was solid in only four starts as a 4-year-old, but could not match the excellence she enjoyed at 3. Equally excellent on both dirt and turf, she won 12-of-17 career starts and is a member of the Hall of Fame in both the United States and Canada.

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2. Skip Away (1996). This American iron horse was the greatest of the Molson/Woodbine Mile winners before the race moved to the turf. A son of Skip Trial trained by Sonny Hine, Skip Away collected 16 graded stakes wins and four Eclipse Awards during his four seasons on the racetrack. In his 3-year-old season he made the most of his only trip to Canada with a four-length romp in the Woodbine Million. It was his fifth stakes win of the season and preceded an upset victory over the great Cigar in the Jockey Club Gold Cup. The champion 3-year-old of 1996, Skip Away would keep it going over the next two seasons with 11 more graded stakes victories, highlighted by a romping win in the 1997 Breeders’ Cup Classic at Hollywood Park. He closed out his career with his best overall season of all in 1998 as the Horse of the Year. Having danced every dance, Skip Away won 18-of-38 races and amassed nearly $10 million in earnings. He was inducted into the Hall of Fame in 2004.

Eclipse Sportswire

1. Wise Dan (2012, 2013). Selecting anyone over Skip Away on this list was not easy, but that is how much respect I have for the great gelding Wise Dan. He was at his best on the turf, but he could run with anyone on any surface and was remarkably consistent from 2010 through 2014. A winner of 19 graded stakes overall, the Charlie LoPresti-trained star will best be remembered for his mile grass performances, which included back-to-back victories in both the Woodbine Mile and the Breeders’ Cup Mile at the ages of 5 and 6. He retired having won 23 of 31 career starts and earned more than $7.5 million over five seasons on the track. Awarded the Horse of the Year title in both 2012 and 2013, he also took home Eclipse Awards for Champion Older Male and Champion Male Turf Horse in both of those years. He is the only horse in history to win the same three Eclipse Awards in consecutive years. Wise Dan was inducted into the Hall of Fame in 2020.