On a weekend of huge upsets, the GIII Rood & Riddle Dowager Stakes proved no different as 14-1 longshot Malibu Smart (English Channel) emerged from the late scramble to win the turf marathon feature Sunday afternoon at Keeneland.The fillies and mares broke in a line with Pretty Tapit (Tapit) and Modarosa (Palace Malice) going right to the front. In a similar tactic to her last start, Modarosa looked eager to lead midway on the first turn and remained at the head of affairs for most of the running. Malibu Smart watched those two from the fence in third while Speed Shopper (Quality Road) tracked in sixth from cover and positions remained consistent through the second turn. 3-1 shot GISW Fionn (Twirling Candy) was still near back as the tempo quickened up front and Pretty Tapit tried to get closer to Modarosa heading into the far turn.The race changed dramatically on that final bend as Pretty Tapit dropped out of contention and Modarosa grew leg weary, allowing Somethinabouther (Mendelssohn) to rally briefly into the lead from the middle of the course. Meanwhile, after going around the fading longtime leader, Malibu Smart found a second wind via the inland route to kick away from the cavalry charge.The chestnut hit the wire in front with air to spare as Fionn rolled late for second and Speed Shopper closed the trifecta in third.The final time was 2:33.27.A former claimer turned graded winner, Malibu Smart is now on a three-race win streak at the Dowager distance. She was last seen Aug. 29 defeating optional claimers at Kentucky Downs by over four lengths. springs the upset and wins the G3 @roodandriddle Dowager S. at 14-1!The 6y/o mare is trained by @trainerMMaker and piloted to victory by jockey @_benacurtis.#TwinSpiresReplay https://t.co/zxGilJMIpZ— TwinSpires Racing (@TwinSpires) October 18, 2026Sunday, KeenelandROOD & RIDDLE DOWAGER S.-GIII, $346,250, Keeneland, 10-18, 3yo/up, f/m, 1 1/2mT, 2:33.27, gd.1–MALIBU SMART, 122, m, 6, by English Channel 1st Dam: Mooghareadh, by Malibu Moon 2nd Dam: Blue Moon (Fr), by Lomitas (GB) 3rd Dam: To the Rainbow (Fr), by Rainbow Quest1ST BLACK TYPE WIN, 1ST GRADED STAKES WIN. O-Hui, Michael M. and Forte, Phil; B-Shadwell Farm, LLC (KY); T-Michael J. Maker; J-Ben Curtis. $200,725. Lifetime Record: 30-4-8-5, $611,029. Werk Nick Rating: B. Click for the eNicks report & 5-cross pedigree or free Equineline.com catalogue-style pedigree.2–Fionn, 122, f, 4, Twirling Candy–Gaelic Gold, by Giant's Causeway. ($75,000 Ylg '23 KEESEP). O-Messina, George and Lee, Michael; B-Dixiana Farms LLC (KY); T-Brad H. Cox. $64,750.3–Speed Shopper, 124, m, 5, Quality Road–Fast Retailing, by Malibu Moon. ($430,000 Ylg '22 KEESEP; $95,000 RNA 3yo '24 KEENOV). O-Barber, Gary, Bridlewood Farm and Eclipse Thoroughbred Partners; B-AR Enterprises, LLC. & Edward Easton (KY); T-William Walden. $32,375.Margins: 1 3/4, 1 1/4, HF. Odds: 14.70, 3.41, 3.30.Also Ran: Massarat, Somethinabouther, Golden Sunshine, Snipsnippitysnip, Sky Low Low, Modarosa, Pretty Tapit, Poppy the Princess. Scratched: Venencia (Fr).Click for the Equibase.com chart or the TJCIS.com PPs. VIDEO, sponsored by FanDuel Racing.The post Another Big Upset at Keeneland as Malibu Smart Takes Dowager appeared first on TDN | Thoroughbred Daily News | Horse Racing News, Results and Video | Thoroughbred Breeding and Auctions.