Wynne decided to pursue an athletic career of his own as early as the age of six, choosing soccer over his father's sport, baseball.

[7] He underwent surgery for an enlarged aortic root,[8] but was unable to secure medical clearance to return to the game, and officially announced his retirement as an active player on April 20, 2018.

Wynne was an integral part of the U-23 side that earned qualification to the Beijing Olympics, which also included, then Toronto FC teammate, Maurice Edu.

Wynne received his second cap for the senior team on January 24, 2009, against Sweden, drawing a penalty that Sacha Kljestan converted.

After retirement, Wynne moved to Quincy, Illinois, where he served as the assistant coach of the men's soccer team at John Wood Community College[10] until 2021.