The Mathews Cup was presented by Charles Mathews who was Club Captain in 1948. He was a jeweller and had a shop on Chesham High Street. Several of the Mathews family played golf at Ley Hill. Mrs M.Mathews was Lady Captain in 1963.

The Matthews Cup is a doubles matchplay competition, usually played in foursomes format, and run throughout the summer. Until 2019 the final was played over 36 holes, although more recently the final is played over 18 holes. No pairing has managed to defend this title for over 25 years.