On 22nd October 1910 when the clubs met for their first ever match , Hugh Ramsey scored in a 3-0 win for the Honestmen. This first ever encounter between the two clubs was notable for the operation of Ayr United's first ever sponsorship deal.
Ayr tailors, Stewarts of 224 High Street, Ayr had offered to provide an overcoat to any player who scored two goals in a home league match, two coats for four goals and so on. Another member of the public of the players choice would also receive such a coat. The deal not only rewarded the player who scored, but provided a huge incentive to United players to score in home matches.
The first ever match between the two clubs at Cowdenbeath was held on 19th November 1910 when the local team won by 5-1, when Cowdenbeath played at North End Park. United had an early win on 9th April 1955 by 2-1.
Central Park, however, was the venue when the scoring was reversed on Sunday 27th January 1974 for the Scottish Cup match. Not only was it an important cup match for Ayr, but this match was also the first ever Sunday match to be played in Scotland. Ayr celebrated the event with a resounding 5-0 win.
The league match on 11th April 1987 ended in a 3-1 win for Ayr but this was not enough to see Ayr regain first division status that season. However, the 6-1 win on 12th September 1987 was the beginning of Ayr's return to the first division in a season when they won the 2nd division championship.
Cowdenbeath themselves had moved into first division football by the time the Ayr played them at home on 6th March 1993, a rather poor game which Cowdenbeath won 1-0. Ayr reverse the score by winning 1-0 on 17th April 1993 at Central Park.
On 15th September 2007 United extended an unbeaten run to six early in the season when Alex Williams swivelled on a Moore cross to hit a cheeky 69th minute shot over his shoulder and into he top corner of the net earning 1-1 draw at Central Park.
On 2nd December 2007 Cowdenbeath crushed 10-man Ayr with a ruthless display of attacking football at Somerset Park.
The Honest Men took the lead through op scorer Alex Williams before the 'Blue Brazil' equalised through Pat Scullion's bullet header from 10 yards. Douglas Hill headed Cowdenbeath into the lead on the hour mark and Mark Ramsey made it 3-1 with a close-range strike to stun the hosts. Ayr's misery was compounded when Mark Casey was sent off and John Armstrong made it four with an 18-yard drive.
On saturday 5th January 2008, United have a six pointer to win a match that would take them out of the relegation drop zone.