Winitsky started playing tennis at the age of eight and was a highly successful youth player. In 1977 he won the title at the junior tournaments of the Wimbledon Championships and the US Open , as well as the national junior championship of the USTA, with victories over Ivan Lendl and Yannick Noah . He stood in front of John McEnroe in the ITF Junior World Ranking, which was published for the first time this year . In total, he won the Orange Bowl three times . He attended Piper High School, studied at UCLA, and was named to the All American top pick .
In 1978 Winitsky became a professional tennis player and was able to win three double titles with changing partners in his first year on the ATP Tour . In 1981, three more double titles followed, as well as his first title in singles, at the tournament in Hong Kong he defeated the Australian Mark Edmondson . 1982 was his most successful year on the ATP Tour, with three more double titles and two single titles. In the course of his career he was able to win a total of three singles and nine doubles. He reached his highest score in the tennis world rankings in 1982 with position 35 in singles and 1983 with position 7 in doubles.
His best individual result in a Grand Slam tournament was reaching the third round at the French Open and the US Open. In 1983 he was in the doubles competition alongside Fritz Buehning in the final of the US Open, the game against Peter Fleming and John McEnroe was clearly lost in three sets. In the mixed competition, he reached the quarter-finals at the 1980 US Open alongside Rayni Fox .
In 1985 Winitsky ended his professional career at the age of only 26 due to a protracted shoulder injury. From 1991 he played again in satellite tournaments and occasionally received wild cards for qualification in ATP tournaments. He played his last tournament in 1997 on the ATP Challenger Tour , but at the tournament in the Bronx he failed in the first round of qualification. Between 2001 and 2005 he played on the ATP Seniors Tour. Here he won the national over 40 hard court championship in 2003 and was ranked 9th in the world in October 2004.