[4] Winkelman grew up as a supporter of his home town club, Wolverhampton Wanderers before his eventual involvement with Wimbledon and ultimately Milton Keynes Dons.

[1] In 2001, in a deal facilitated by Winkelman, the Wimbledon FC board of directors decided to relocate the club to Milton Keynes, around 60 miles from its south London home base.

[9] In August 2024, Winkelman sold the club to a Kuwait-based consortium, with Fahad Al Ghamin replacing him as chairman.

[11] Winkelman moved to Milton Keynes in 1993,[12] establishing Great Linford Manor (a 17th-century mansion) as a recording studio complex.

[13] In June 2013, Winkelman was awarded an honorary doctorate by the Milton Keynes-based Open University "to mark his contribution to education through the world of professional football".