Winston is winner of numerous international and national competitions. Most recently, he won 1st place in the Orleans Concours International, held in France. His prize engagements include recital and concerto appearances in France and Spain, as well as recording contracts with Harmonia Mundi and Quadro Frame. He also won 1st place in the Soloist Division of the 2000 International Krystof Penderecki Competition. He is one of the few two-time winners of Indiana University's Piano Concerto Competition, and has also won the grand-prize of the 2000 Indianapolis Matinee Musicale, the 2000 Kingsville Piano Concerto Competition, and the 1999 Crane Festival of NewMusic Solo Performer Competition.
Winston performs frequently in solo recitals, as a collaborative pianist, chamber musician and concerto soloist. He has also been featured on radio for WFIU (Indiana) and WFMT (Chicago) in live and recorded broadcasts. New York audiences first heard him when he played with flutist Ken Chia in their New York debut at Carnegie-Weill Recital Hall. His concerts have brought him to venues in Poland, the Netherlands, China, Malaysia and Brunei. Orchestras he has been featured soloist with include the Peninsula Music Festival Orchestra, the Royal Conservatory of Music of Toronto Symphony Orchestra, the North Toronto Collegiate Institute Symphony Orchestra, the Indiana University Concert Orchestra, and the Fort Collins Symphony Orchestra.
He is also actively involved in the performances of contemporary music, playing in numerous new music festivals and conferences. In April of 1999, he performed Post-Partitions by Milton Babbitt for the composer's induction into the American Classical Music Hall of Fame in Cincinnati, Ohio. He has premiered dozens of new works and has had numerous works dedicated to him. Composers he has worked with include Leslie Bassett, P.Q. Phan, Sven-David Sandstrom, and Elliott Carter.