I am informed by Mr. A. C. Morrish, the energetic Secretary of the League, that he has been able to arrange with the Directors of Barry AFC for the first round of the Barry Cup Competition to be played at Jenner Park, Barry, on Saturday next when Barry Bohemians will meet Barry Centrals. Some good football will no doubt result from the meeting of these teams, who proved themselves strong combinations so far this season.
Barry Dock News, Friday 5th November, 1920
That 1st Round Draw in full was;
A. Cadoxton Old Boys v Cardiff Corinthians Reserves
B. Aberthaw & Rhoose v Splott Amateurs
C. Barry West End v Barry Y.M.C.A.
D. Barry United Churches v Penarth Y.M.C.A.
E. Penarth Parish Church v Barry Y.M.C.A. Athletic
F. Barry Bohemians v Barry Centrals
Byes : Penmark Rovers to play Winner of F, Sully to play Winner of D.
Ties played 1st November, 1920.
As it turned out, the eventual first ever Barry Cup Final, between Cadoxton Old Boys and the Barry YMCA, had to be replayed the following season following accusations of ineligible players on both sides. Cadoxton O.B. won the original Final 3-2, at Jenner Park, and the re-match in September 1921 resulted in a more emphatic 3-0 win for Cadoxton.
By then, Cadoxton Old Boys had changed their name to simply Cadoxton AFC and managed to get to the Barry Cup Final again in April 1922, this time swamping Barry Island's Whitmore Albion 7-1.
This was the only time that, technically, two Barry Cups were played for in the same season. Cadoxton AFC then went on to join the embryonic South Wales Amateur League. So there.