Winter previously served as a football official for the National Collegiate Athletic Association (NCAA).
His final game as a collegiate official was the 1995 Orange Bowl, when Nebraska defeated Miami 24–17 concluding a 13–0 season and winning a national championship.
He entered the NFL as a line judge in 1995, and later was promoted to referee in 1998 after Dale Hamer returned to the head linesman position and Gary Lane returned to the side judge position.
During the game back judge Scott Green did not realize that New York's Rich Seubert had lined up legally in a receiver's spot and failed to call a defensive pass interference foul against him during a failed field goal attempt, instead penalizing him for ineligible receiver downfield.
Commissioner Paul Tagliabue described the situation as the most disappointing officiating blunder he had seen in his years as NFL commissioner[3] and announced there would be changes in the officiating of field goal attempts and during the last plays of games.