Rugeley-based Wynter has been involved with a number of Staffordshire-based clubs during his junior years, including Stoke City, Stone Dominoes and Hednesford Town, before taking the chance to further his development as a teenager with a spell in the United States with Kansas City-based side Blue Devil Athletic

After returning to the UK, Wynter linked up with Stafford Rangers in the summer of 2014, playing a handful of games for the NPL Division One South side.

At the end of the season, he made the switch to Mickleover Sports, but only featured in pre-season for them before leaving in September 2015 to join Chasetown

He enjoyed a consistent season at Chasetown, scoring 9 times for the Scholars before re-joining league rivals Stafford in February 2016.

Whilst at Marston Road, Wynter was part of the Rangers side that clinched promotion back to the NPL Premier League at the second time of asking

Wynter returned to Chasetown in July 2016, playing over 40 times for them in the 2016/17 season and scoring 9 goals.

He then made the switch back to neighbours Hednesford in May 2017, but he returned to the Scholars Ground once more in September 2017 after a brief spell at Keys Park.

He made 41 appearances for the Scholars in 2019/20, scoring 4 goals.