Once again the season began with high pe-season expectations of Ayr United success which took a dent in an early exit from the Lower Divisions Cup by a club from a lower division than that of Ayr, East Stirlingshire doing the damage, and the news that once again the Stadium plans would be on hold due to the failing economic climate
Nevertheless United began the league season well and went to the top of the league by mid-August with ace striker Bryan Prunty taking the honours. Good results continued into August and despite a home draw with Brechin, United still kept top spot into mid- September from Peterhead in second.
Tradionally October is a bad month for Ayr and this season was no exception with a disappointing Ayr recording only two wins in six matches putting them in third place by the beginning of November, but still only three points behind Brechin City and Raith Rovers.
Ayr striker Bryan Prunty notched up a hat trick and his 12th goal of the season in a 3-0 win at Hampden Park ensured that Ayr maintained that pressure on the leaders. Over the next few weeks United built on their improving performances and were only 1 point behind the leaders.
Scottish Cup day arrived and United's match against non-league side Lochee United was postponed. In all it was postponed five times, the sixth occasion a late goal gave the Dundee club a well earned draw.
Back in the league United lost ground with a bad 3-0 defeat at Peterhead. Nevertheless by the time that United met at Brechin's Glebe Park on 30th December 2008 the two clubs were occupying 2nd and 3rd place. United's 1-0 win through top scorer Bryan Prunty tightened Ayr's grip on 2nd place closing the gap on Raith Rovers to one point going into 2009.
The Scottish Cup provided Ayr with a break from the hectic league campaign again although a tie against Kilmarnock is never something that can be taken lightly. The Cup had acquired the Homecoming label to mark the celebrations for the 250th anniversary since Robert Burns' birth. It was inevitable, therefore that not only would there be an Ayrshire Derby in the competition but Ayr themselves would be make an impression.
The 4th round tie saw Ayr's best laid schemes go awry with Kilmarnock scoring their first competitive goal against Ayr in four previous cup outings. United were not going to lie down easily and replied within five minutes. Killie snatched a second half lead with Ayr missing a few certainties in front of goal. The game was slipping away from Ayr when Kilmarnock were awarded a penalty with 15 minutes remaining. A lamentable penalty from Alan Russell was easily saves by Stephen Grindlay who smothered the strikers muffed shot gratefully. Despite an early Prunty goal which put Ayr ahead in the replay at Rugby Park, Killie's Premier League quality came through as they eventually won by 3-1.
United bounced back with a good home win against Arbroath in the league but the cup games meant thgat Ayr were now seven points behind leaders Raith Rovers albeit with games in hand. The two met at Somersedt Park at the end of January and Ayr missed the opportunity to cvlose the gap by only managing a 2-2 draw, albeit having been 2-0 down.
United threw away points by losing at Alloa when again top spot was within their grasp. Raith were also faltering but United found themselves 2-0 down the following week at home to Brechin City, but recovered to win by 4-2 and a 3-0 win at Hampden Park in late February put Ayr one point behind Rovers with a game in hand. Ayr were going for top spot early in March with a home weekday match against Queens Park and things looked grim when the Glasgow club took the lead. United found an equaliser and the resultant point, though disapointing, put Ayr at last on top of the division by a slender margin. In fact the clubs were exactly level, same number of games played, same points and the same goal difference.
It gave Ayr heart and they trounced relegation threatened Stranraer by 5-0 on 7th March and although Rovers won United at last opened up a margin of 4 goals at the top. The top of the table clash saw United beat Raith Rovers 1-0 at Kirkcaldy the following week and the scene was set for a hard fought run in.
The two clubs kept up their winning run and by the time that Ayr met Brechin City at Glebe Park on 18th April they had been on a ten match unbeaten away run. However hearts were broken as a rather under strength City beat Ayr 1-0 allowing Raith Rovers to hit top spot. A further laps of concentration brought about a 1-1 draw at home to Alloa and the title dream was over. United settled for a play off place and finished the league season with a 3-2 win at Peterhead, a notoriously difficult place for Ayr to pick up points.
Ayr United entered the play off's for the first time on 13th May 2009 with an excellent 2-0 win at Brechin's Glebe Park in the 1st leg and followed this up with 3-2 home win in the 2nd Leg. The final matched Ayr with Airdrie United who were in the play off's to retain their first division status - a proze that Ayr were as keen to take for themselves.
The clubs lined up at Somerset Park but despite a good start for Ayr, two absurd lapses in their defence gave Airdrie a 2-0 lead at half time. However Ayr's character and their habit of winning from such situations throughout the season proved invaluable as Mark Roberts scored twice early in the second half to bring the scores level. A golden opportunity was squandered when Chris Aitken missed a penalty late in the match. Airdrie, who had lost the final on the the two previous seasons almost looked a beaten side as the clubs trooped on the Exclesior Stadium for the 2nd Leg. It was inded Ayr who drew first blood when Ryan Stevenson hit a 20 yarder which curled into the Airdrie net to give Ayr a 1-0 lead on the half hour.
The chances went Ayr's way as Airdie heads fell and the final whistle brought Ayr United an end to their five year wait to re-enter the First Division.
With the prospect of a few new faces at Somerset Park and hopefully new life thrust into stadium plans, 2009/10 could be good year for Ayr United in their build up their centenery celebrations.