[5] Winstanley spent over 20 years on the coaching staff at Barnsley,[6] but left in June 2001, which ended a 34-year association with the club.

[8] Winstanley became technical director of the Saint Kitts and Nevis national team in 2001,[9] before leaving in February 2004.

[citation needed] Winstanley was brought into the Scarborough coaching staff as assistant manager in October 2005.

[6][11] He left the position in July 2006 following Mark Patterson's arrival onto the coaching staff and became the York City head of youth development in October.

[14] He joined South African team SuperSport United as technical director of the club's development wing in October 2009.