The Middlesex FA Senior Challenge Cup is contested by the most Senior clubs in the County and is considered by many as the most prestigious competition in Middlesex. 

Established: 1888

First winners: Clapton FC

Most Senior Cup titles: Hendon FC (16)

Current holders: Rayners Lane

Fun fact: Enfield FC won the competition for four years running between 1977-1981, winning each final by the same scoreline - 2-0