The Challenge Cup is noted in society records as having been donated in 1926 by Gerrard F. Thornton (Club member from 1906 to 1957). This makes it one of the two oldest society trophies (along with the Duncan Collie Medal). However, the Cup is only engraved from 1961 so the history prior to that is not clear.
It is now played for as a combined trophy over the season and is presented at the Annual Dinner. The winner is a player with a handicap in Division 2 (Handicap Index of 16.0 or above), who has the best 3 rounds from 5 from the Spring, Summer and Autumn Meetings, and from day 2 and day 3 of the Summer Tour, other than the winners of the Bill Wood Jug, Allinson-Parkhill Trophy and Christie Bowl.