The draw for the first edition of the competition was held at the Montpelier Hotel in Bristol on 5 October 1887 and featured seven entrants.

There was a growing feeling among teams participating in the tournament that the dominance shown by City and Rovers meant that all other entrants were going into the competition each year knowing that they had no hope of winning.

A solution to this problem was put forward at the annual meeting of the Gloucestershire County Football Association (GFA), held at the Crown & Dove Hotel in central Bristol on 2 August 1907.

The change in the format of the competition coincided with a move from the final's traditional place in the calendar on Easter Monday, enabling more flexibility with the scheduling of matches.

^[α] The 1908–09 final was held over to the beginning of the following season due to fixture congestion suffered by City.