Maypray played college football at Virginia Military Institute (VMI) where he played several different positions (wide receiver, running back and quarterback) and returned kicks.[2] During his four-year career at VMI, Maypray scored 39 touchdowns.[2] Maypray was named the 2006 Big South Freshman of the Year.[3] He was named First Team All Big South at kick returner, and Second Team All Big South at wide receiver after his sophomore season.[3] Heading into the 2009 season, Maypray received several pre-season honours including being named to the Big South Football Conference Pre-Season All Conference Team at both quarterback and as a punt returner.[4] He was also voted the 2009 Big South Pre-Season Offensive Player of the Year.[4]
Professional
Maypray made his professional debut with the Montreal Alouettes of the Canadian Football League (CFL) during the 2010 season. During his first game, Maypray returned a missed field goal by Luca Congi of the Saskatchewan Roughriders 125 yards for a touchdown, setting a team record.[2] During the Alouettes next meeting against the Roughriders, Maypray returned another missed field goal 118 yards for a touchdown.[5] After his second missed field goal return for a touchdown, Maypray was named the CFL's Special Teams Player of the Week.[6]
Off Season
During the off season of the CFL, Maypray worked at his old high school, Randolph-Macon Academy.
Personal life
While at VMI, Maypray also played on the basketball team.[3] He majored in psychology.[3]