The popular veteran rider was mobbed in the winner's circle by fellow jockeys and well-wishers after scoring the half-length victory aboard Gracelicious for trainer Debbie England and owner Formal Racing Stable.
"I would just like to thank all of the people that helped put me on some nice horses to get 2,000 wins," said the 45-year-old Dos Ramos.
Gracelicious paid $3.70 in the seven-furlong maiden allowances race for fillies and mares.
Dos Ramos, who ranks second among Woodbine regulars in years of service behind David Clark, began his riding career in 1981, winning his first race aboard Lord Henry on April 20, 1981, at Greenwood. He went on to capture the Woodbine and Greenwood fall meets en route to a Sovereign Award title as the nation's top apprentice jockey. He captured another Sovereign after a 162-win season in 1982.
"Dos" guided two horses to key victories at Woodbine en route to their Horse of the Year titles. In 1992, Benburb upset A.P. Indy in the Molson Export Million. Thornfield scored the Canadian International in 1999 before earning championship honors. He has three Oaks victories (Carotene, 1986; Plenty of Sugar, 1994; Ginger Gold, 2002), plus wins in the Breeders' Stakes (Carotene, 1986), the Coronation Futurity (Bold Executive, 1986) and the Princess Elizabeth (Super You, 1989; Ginger Gold, 2001).
He finished second aboard Sir Khaled in the 1983 Queen's Plate.
Dos Ramos received the Avelino Gomez Award for significant contributions to the sport in 2002.