Winston is a highly ranked USTA tennis player sponsored by Wilson, and a 5x Tour Player of the Year in golf.


Winston excelled at the 10u Boys singles achieving #1 MAS ranking and a sponsorship by Wilson. Winston has since achieved #5 MAS ranking in the 12u Boys singles and #9 12u Doubles with a Wilson full sponsorship renewal. Winston is also a highly ranked national singles player (#60) and has been selected as part of the USTA Player Development team since age 10. Winston was also selected into the Excellence Team (based on tennis ranking, academics, community service) since age 10 and was selected for 3 years consecutively with USTA scholarships to compete at the International Orange Bowl in Florida where they gave him all-expense paid trips (2014, 2015, 2016) to travel with his team of coaches. Through the Excellence Team, Winston is very involved in community service to help underprivileged kids in the D.C. community. Winston is currently ranked #17 14u MAS (as of 2/28/18).

Winston was invited to compete in the 2016 National Spring Team Championships in Mobile. Alabama.


Winston is 5x Tour Player of the Year in Golf. He has qualified and competed in the US Kids Golf World Championships at Pinehurst every year since age 6. He has also competed in the European Championships in Gullane, Scotland for several years and has also qualified to compete at several tournaments such as Doral, Seaview, Copperhead, PGA National and Venice Open, Italy. Winston was runner up in 2016 Augusta National’s Drive Chip & Putt competition.

Sidwell Varsity Golf Team Wins 2018 MAC Championship