The 1999/2000 season was the 103rd season of Scottish league football.
A 7th position is as much as Gordon Dalziel,s men could manage for the season with a wild variation in scores ranging from a 5-1 defeat by Raith Rovers in September to a 5-0 win over Airdrie in December.
On the park, the club was gaining a reputation as a Cup side and Premier League clubs Motherwell and Dundee suffered at the hands of the Honest Men during the season.
The excellent Scottish Cup run came to a disastrous end in April with a 7-0 defeat by Rangers in the semi-final at Hampden Park.
Nevertheless the run involved an epic match at Motherwell in the 4th round in which Ayr beat their Premier league opponents by the odd goal in seven.