[6] While attending the University of Charleston, Windster also played semi-professional football for the Southern West Virginia King's Warriors of the Premier Development League.
[8] The following season, Windster signed for AFC Ann Arbor of the National Premier Soccer League.
In the club's third match of the group stage, Windster scored a goal as Rincon drew Avenues United FC of Saint Vincent and the Grenadines 2–2 in Santiago de los Caballeros, Dominican Republic.
[15] In December 2015, Windster was named to Bonaire’s provisional squad by head coach Ferdinand Bernabela in preparation for 2017 Caribbean Cup qualification.
[17] In September 2018 Windster was named to Bonaire's squad for the inaugural qualifying campaign for the newly established CONCACAF Nations League by head coach Emmanuel Alexis Cristori.