Ciaran Winters became the first player in club history to earn a professional contract after being an academy player. Winters signed his first professional contract ahead of the 2021 season.
Winters signed the first academy contract in FC Tulsa history ahead of the 2020 season. Winters never made a regular season or playoff appearance, but he scored in his lone preseason appearance: a 1-1 draw against Oral Roberts University.
2018-2019 – SPORTING KANSAS CITY (DEVELOPMENTAL ACADEMY), YOUTH
Winters spent the 2018 and 2019 seasons representing Sporting Kansas City's MLS developmental academy accumulating 35 appearances, 23 starts, and a goal over that time.
Winters began playing in the youth soccer system of Tulsa winning three state championships among many other youth accolades. While playing youth soccer, Winters received coaching and tutelage under current FC Tulsa head coach Michael Nsien.