It was a 10 goal thriller the first time these two clubs met on 27th August 1910 at Logie Green in Edinburgh. Charlie Howe scored his, and Ayr United's, second hat trick in a 6-4 away win.
The Honest men made it a double on hogmaney with a 3-1 win at Ayr in the return league match.
On 25th November 1911 Ayr won 3-1 at Leith's Logie Green and Ayr made no mistakes on 23rd December 1911, winning 4-2 at Ayr.
Leith, however, gained some revenge with a 3-0 Scottish Cup 1st round proper win at Logie Green on 27th January 1912.
The following season Ayr recorded two superb wins against the Edinburgh men, winning 3-0 at Ayr on 7th December 1912 and by 4-1 at Logie Green on 22nd February 1913.
Season 1947/48 brought a 1-1 draw Edinburgh but a superb home win on 27th March 1948 when United recorded a superb 5-1 victory.