[1] In the 1950s, the West Indies batsman, Allan Rae, played for Winchmore Hill CC whilst completing a law degree in England.

In July 1949, a tour match organised by Rae between the West Indies and Winchmore Hill was played at The Paulin Ground, featuring players such as Learie Constantine and Everton Weekes.

[1] In 2012, Winchmore Hill CC secured their maiden Premier League title in the penultimate game of the season against Ealing Cricket Club.

[6] The club boasts 3 cricket pitches with electronic scoreboards, high quality nets and a multi-use games area (MUGA).

Winchmore Hill CC also has a thriving colts section ranging from under 9 to under 17 principally run since 2015 by club Child Development Officer, Jim Clarke.