He joined Dundee Utd in January 1992, and went on to make around 150 appearances for the Tannadice club before Alex Miller brought him to Pittodrie in 1998. Winters was involved in the exchange that took Billy Dodds to United, and in a deal that surprised many and it took Winters some time to settle at Pittodrie. He took over in Goal for the injured Jim Leighton in the Scottish Cup Final in 2000 at Hampden. Aberdeen went on to loose 4-0 to Rangers. 2000-01 saw Robbie arguably enjoying his best spell in an Aberdeen shirt, scoring a hat-trick against his old club in September 2000. He was the top Aberdeen scorer before surprisingly moving to Norway.