Winegar was born in Sarasota, FL and attended Pine View School. At 15, he won the Boys’ 16s doubles title at the USTA International Spring Championships in Carson, California. He played NCAA DI doubles at
Columbia where he was a four-time D1 Scholar-Athlete for the Columbia Lions. At Columbia, he was twice named First Team All-Ivy and an NCAA All American partnering with
Michael Zheng and
Max Westphal. He reached the Elite 8 at the ITA Fall Nationals with Westphal in his sophomore year and was ranked in the ITA National Top 10 twice. Winegar finished his senior season ranked No. 1 in the ITA Northeast Region and No. 24 in the ITA doubles with Zheng. He graduated with a bachelors degree in psychology. Winegar played a post-graduate year for the
Duke Blue Devils where he and partner
Cooper Williams finished as Top Ten ITA All- Americans. They won the inaugural American Collegiate Wildcard Playoff in Orlando, FL to earn a spot in the main doubles draw of the
2025 US Open. ==Professional career==