Vale of leven had alread a history of Scottish Cup wins by the time Ayr United played their first ever match with them on 10th September 1910 at Somerset Park, the 2nd division match ending in a 2-2 draw.
Ayr United achieved the first win between the two clubs on Christmas eve 1910 with a 2-0 win in Dunbartonshire.
The following season saw United record an excellent 3-2 win at Milburn Park in the 2nd division match but the return match at Somerset Park on 11th November 1911 was abandoned after 71 minutes with the score at 1-1. The fact that the match ran out of light was due to the Vale of Leven team arriving late because of a railway accident. The match was not replayed.
In August of the following season Ayr swept Vale of Leven aside with a superb 6-0 win at Ayr and followed this up later in the season with a 3-1 win at Millburn Park on 1st March 1913.