Overpass can become the first three-time winner of the Group 1 Winterbottom Stakes at six furlongs at Ascot Racecourse in Perth, Australia, early Saturday if he can beat the fierce closer Jokers Grin. Overpass, a winner of 10 of 33 starts, has thrived at Ascot, winning 4 of 5 career appearances there. Aside from the Winterbottom in 2023 and 2024, Overpass won the $2.6 million Quokka Stakes at Ascot in April 2023, a six-furlong sprint with a field determined by owners who purchase berths and then name a starter. A 7-year-old gelding, Overpass has been beaten in his last four starts, including a fourth-place finish by 1 1/2 lengths in the Group 1 Everest Stakes at six furlongs at Royal Randwick Racecourse in Sydney on Oct. 18. The $13.09 million Everest is the world’s richest sprint. Jokers Grin, a 5-year-old gelding, has won 9 of 12 starts, including seven races at five furlongs. In his only start at six furlongs, Jokers Grin won the $3.19 million Quokka Stakes at Ascot in April, closing from 12th of 13 to win by about a neck at 20-1. :: Get free past performances, analysis, and picks for international racing, including Australia Jokers Grin has won two Group 3 races at Ascot – the Prince of Wales Stakes at five furlongs on Nov. 1 and the Colonel Reeves Stakes at 5 1/2 furlongs on Nov. 15, closing from well off the pace. Jokers Grin was the 3-2 favorite in early betting for the $977,500 Winterbottom Stakes as of Wednesday, with Overpass at 9-5. The race drew a field of nine, including the Southern Hemisphere 3-year-old filly Luana Miss, who has won 4 of 6 starts. Luana Miss is also a two-time stakes winner this month at Ascot against Southern Hemisphere 3-year-olds, taking the Placid Ark Prelude Stakes at 5 1/2 furlongs on Nov. 1 and the $326,800 Placid Ark Stakes at six furlongs on Nov. 15. Luana Miss, who runs from off the pace, was 10-1 in early betting on Wednesday. :: Want to learn more about handicapping and wagering? Check out DRF's Handicapping 101 and Wagering 101 pages.