The five hopefuls are Annan Athletic, Cove Rangers, Edinburgh City, Preston Athletic and Spartans.
Ayr united have met two of these clubs on previous league and cup business
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Curiously though Annan Athletic produced their own souvenir programme of this event despite United also having produced an official programme, which meant that unusually there were two different programmes produced for the same match.
This must be unique in Footballing history.
Ayr United first visited the Borders town of Annan on 9th July 2005 for a pre-season friendly, winning 1-0 against the local club. Ironically no programme was produced for this match.
Annan invited Ayr United to be part of their Brewers Cup competition the following season and the clubs lined up in the competitions semi-final on 16th July 2006. The local club were not so well prepared this time and United ran out 7-0 winners with Chris Strain getting 2 goals as did Jerome Vareille and G Friels with R Caddis getting the seventh.
A combined programme was produced for the Brewers Cup competition in 2006.
On 15th July 2007 United again met Annan in their Brewers Cup match with Ayr again coming out on top by 5-1. Again a combined programme was produced for the event.
Edinburgh City did not join the league until season 1931/32 but it was not until season 1936/37 that the clubs finally met, on 2nd Division business due to Ayr's relegation the previous season.
The clubs met for the very first time at Somerset park, Ayr on 22nd August 1936 with Ayr winning by 3-2.
14th November 1936 was the date of their first ever meeting in Edinburgh with Ayr United winning by a large 4-1 margin at Pilton Park.
With Edinburgh City not returning to the league after the war these matches are the only times that the clubs have met on league business.
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However, the clubs met on 11th December 2004 in a Scottish Cup business at Somerset Park where two late goals eased Ayr through to a Third Round clash with Stranraer after the plucky Edinburgh City threatened to cause an upset at Somerset Park.
In 24 minutes Ayr got their breakthrough when Gilmour picked out the unmarked Ferguson who buried a textbook header into the bottom corner of the net. The expected floodgates didnt open and it was not until 70 minutes when a Conway corner was only half cleared to Ferguson and his shot was too hot to handle for Mackintosh, allowing Henderson to slam home the rebound from six yards.