With both clubs in a dog fight for the automatic promotion place both are keen to gain advantage in this re-arranged fixture.
The first match between the two clubs occurred on 31st October 1936 and Ayr United asserted their authority on that match, winning by 8-1, still the highest aggregate between the two clubs.
Taking the long road to Angus has been something that Ayr United has done since the first match at Brechin's Glebe Park on 23rd January 1937 where a 3-2 second division win for the Honest men eased the journey.
Another Scottish League Cup win occurred on 1st September 1954 where Ayr recorded a 4-2 win that day and backed that up with a 3-0 win a ·B· division encounter later that season on 13th April 1955.
City recorded their first win against United on their own soil on 3rd March 1956 when they won the ·B· division clash 1-0. Another league cup meeting on 10th August 1957 brought City a good 5-2 win, but it was Ayr who hit 5 in the 2nd division league meeting on 1st March 1958 in a 5-3 win.
First division football for Ayr meant that the two did not meet again until another 2nd division clash on 7th April 1962 and Ayr tucked away the points after a close 4-3 win. A 2-1 win for Brechin the following season only made the way for another close 4-3 win for Ayr on 8th February 1964.
United·s next win at Glebe Park came in another league cup pairing on 28th August 1965 when they won 1-0 and Ayr confirmed their winning ways there in their promotion year by winning 2-0 on 6th April 1966.
By the time that Ayr lost 5-1 at Brechin on 10th April 1968 the first division had come and gone but it was on its way back when the Honest Men won convincingly by 3-0 on 12th April 1969.
League reconstruction had bedded in the by the time that the two met again, this time in a new look first division on 24th September 1983 and Brechin won 2-1.
First division football had slipped from both clubs by the time they met next, this time during Ayr·s championship winning year on 19th September 1987 and a good 3-0 win was achieved by United. Brechin did win 2-1 on the last game of the season, by which time Ayr were on their way to division 1.
Brechin had made their own way to Division 1 for a 2-1 defeat on 15th September 1990 and a 2-2 draw on 23rd March 1991. The same season Ayr had punished City 4-0 at Somerset Park on 19th January 1991 - George Burley's first home match as manager. Ally Fraser, Ally Graham and two from Sammy Johnston did the damage.
It was another win for Ayr on the next visit to Glebe Park, again for a first division clash, on 11th September 1993 and again by 4-1 on 5th February 1994.
It was a season of 1-1 draws when the two met again, second division football blighting the two clubs by the time. Steve Kerrigan did the business for Ayr on 24th August 1996 and P Smith on 22nd January 1997.
It was a challenge cup match on 15th August 2000 that took Ayr north again and this time McGinlay could not stop Ayr from suffering an embarrassing 3-1 loss.
A 3-0 win for United on 3rd April 2004 could not stop both clubs being relegated to the Second Division.
A 5-0 win for Brechin early in season 2004/05 defined a season that saw them promoted but Ayr remaining solidly in division 2.
Relegation for City saw the teams line up on 23 September 2006 at GlebePark for the first season 2006/07 encounter.A 2-0 win for Ayr was the result. With both teams pushing for a play off place Brechin's form had slumped. However a 1-1 draw suited the Angus team and United's play hopes had gone.
On 18th August 2007 the teams met for the first match of the new season and at Glebe Park. Goals in 7th and 77th minute goal from Micheal Moore and Ryan Stevenson gave Ayr a 2-2 draw.
A 2-2 draw was had by Ayr at Brechin on 28th August 2007 and United went one better - winning 2-1 at home on 27th October 2007. However, the two clubs were lying equal second bottom by 29th December 2007 when they met at Glebe Park. The six pointer went City's way with a thumping 5-1 victory over the Honest men. United also lost 3-0 at Somerset Park on 23rd February 2008 to complete a miserable season against the Glebe Park men.
Hopes of a better season in 2008/09 were dented when Ayr could only manage a 1-1 at Somerset Park on 29th September 2008. United must deliver tonight.