Winsor was born in Nottingham, and played for the local rugby team's under 16 level. He trained at Guildhall School of Music and Drama's Central School of Ballet, getting cast as a Liquorice Allsort in the TV movie NutCracker shortly after graduating. In 2008, Winsor starred as one of the background dancers in Lily Allen's music video for "The Fear".
In 2010 came Winsor's first film role as Tomas in StreetDance 3D, which was both a commercial and critical success. His success in film led to supporting roles in the drama series Hollyoakes and Eve in 2011 and 2013, respectively. In addition to his television and film work, Winsor starred in the stage performance of Swan Lake in 2012.
In late 2012, Winsor auditioned for the role of Harry Tressler on Holby City. He lost out on the part to Jules Knight, although the producers expressed interest in working with Winsor in the future. He auditioned for the role of Caleb Knight on Casualty in 2013, and was offered the role later in the year. He began filming in that September, making his first on-screen appearance in January 2014. Winsor made his final appearance as Cal on 29 April 2017, when his character was killed off.
|2003||NutCracker||Liquorice Allsort||TV movie|
|2008||The Fear||Dancer||Music video|
|2010||StreetDance 3D||Tomas||Starring role|
|2011||Hollyoaks||Father Francis/Nathan Harker||Recurring role|
|2012||Swan Lake||The Swan/Stranger||Musical|
|2014-17||Casualty||Caleb "Cal" Knight||Series regular|