Winogradsky played 1983 to 1984 on the ITF Junior Tour, and reached the quarterfinals at the junior tournament of the Wimbledon Championships in 1984, among other things by defeating Patrick McEnroe , where he was defeated by Brad Pearce . He made his first appearance on the ATP Tour in March 1985, when he made his first professional appearance at Wimbledon in the same year, he was eliminated in the first qualifying round. He was able to celebrate successes above all in doubles, and he achieved his first respectable success in 1986 in Metz , where he and his partner François Errard advanced to the semi-finals. At the side of Nathalie Herreman , he reached the second round of the French Open in mixed . In 1987 he was initially on the ATP Challenger Tour with changing partners . At the French Open, he managed an unexpected outsider second round victory over Stefan Edberg . The year 1988 was not very successful, he had his best result in singles when he lost to Patrik Kühnen in the quarter-finals in Brussels .
His most successful years would be 1989 and 1990. At the doubles competition at the French Open in 1989 he sensationally reached the finals alongside Mansour Bahrami , although they did not meet a single seeded pairing until the finals. The title ultimately went to number 4 seeded Americans Jim Grabb and Patrick McEnroe after four sets . Winogradsky won his first title with Bahrami in October 1989. In the same year he won his only individual title at the Challenger tournament in Valkenswaard . He won his second and last ATP double title in 1990 with Javier Sánchez in Kitzbühel . In the following years he played again on the ATP Challenger Tour and sub-class satellite tournaments. In 1991 he had his last notable success when he won the doubles competition at the Challenger tournament in Seville alongside David Rikl . His last tournament was the Miami Masters in March 1994, where he clearly failed in qualifying with 0: 6 and 1: 6 to Roger Smith .
In the course of his career he was able to win two double titles. He reached his highest ranking in the tennis world rankings in 1987 with position 89 in singles and in 1990 with position 17 in doubles. His best individual result in a Grand Slam tournament was reaching the third round of the French Open 1987. In the doubles competition, he reached the final of the French Open 1989. In Wimbledon 1989 and the Australian Open 1990, he was also in the second round of the doubles competition he was in mixed in the round of 16 of the French Open 1986.
Winogradsky worked as a tennis coach after the end of his professional career. So he took over the then 18-year-old Jo-Wilfried Tsonga and led him to the final of the Australian Open 2008. In 2011 the two separated after seven years of working together.