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1999/00
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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.

1999 00 Ayr Utd MATCH2

Airdrieonians (a) 30 Oct 99

Airdrieonians (a) 30 Oct 99

Airdrieonians (a) 4 Mar 00

Airdrieonians (a) 4 Mar 00

Airdrieonians (h) 11 Sep 99

Airdrieonians (h) 11 Sep 99

Airdrieonians (h) 27 Dec 99

Airdrieonians (h) 27 Dec 99

Celtic (h) 13 Oct 99

Celtic (h) 13 Oct 99

Clydebank (h) 18 Mar 00

Clydebank (h) 18 Mar 00

Clydebank (h) 6 Nov 99

Clydebank (h) 6 Nov 99

Dundee (a) 29 Jan 00 (SC)

Dundee (a) 29 Jan 00 (SC)

Dundee (h) 8 Feb 00 SC3R

Dundee (h) 8 Feb 00 SC3R

Dunfermline Athletic (a) 22 Jan 00

Dunfermline Athletic (a) 22 Jan 00

Dunfermline Athletic (a) 25 Sep 99

Dunfermline Athletic (a) 25 Sep 99

Dunfermline Athletic (h) 11 Apr 00

Dunfermline Athletic (h) 11 Apr 00

Dunfermline Athletic (h) 4 Dec 99

Dunfermline Athletic (h) 4 Dec 99

Falkirk (a) 21 Aug 99

Falkirk (a) 21 Aug 99

Falkirk (h) 11 Dec 99

Falkirk (h) 11 Dec 99

Falkirk (h) 6 May 00

Falkirk (h) 6 May 00

Hamilton Acad (h) 17 Aug 99 LC2

Hamilton Acad (h) 17 Aug 99 LC2

Inverness C T (a) 25 Mar 00

Inverness C T (a) 25 Mar 00

Inverness C T (h) 15 Jan 00 (Post)

Inverness C T (h) 15 Jan 00 (Post)

Inverness C T (h) 28 Aug 99

Inverness C T (h) 28 Aug 99

Inverness C T (h) 7 Mar 00

Inverness C T (h) 7 Mar 00

Keith (a) 26 Jul 99

Keith (a) 26 Jul 99

Livingston (a) 16 Oct 99

Livingston (a) 16 Oct 99

Livingston (a) 29 Apr 00

Livingston (a) 29 Apr 00

Livingston (h) 14 Aug 99

Livingston (h) 14 Aug 99

Livingston (h) 29 Feb 00

Livingston (h) 29 Feb 00

Morton (a) 27 Nov 99

Morton (a) 27 Nov 99

Morton (h) 2 Oct 99

Morton (h) 2 Oct 99

Morton (h) 5 Feb 00

Morton (h) 5 Feb 00

Motherwell (a) 26 Feb 00 SC

Motherwell (a) 26 Feb 00 SC

Oxford United (h) 19 Jul 99

Oxford United (h) 19 Jul 99

Partick Thistle (h) 11 Mar 00 SC QF

Partick Thistle (h) 11 Mar 00 SC QF

Raith Rovers (a) 4 Sep 99

Raith Rovers (a) 4 Sep 99

Raith Rovers (a) 8 Jan 00

Raith Rovers (a) 8 Jan 00

Raith Rovers (h) 1 Apr 00

Raith Rovers (h) 1 Apr 00

Raith Rovers (h) 10 Aug 99

Raith Rovers (h) 10 Aug 99

Raith Rovers (h) 14 Nov 99

Raith Rovers (h) 14 Nov 99

Rangers (n) 8 Apr 00 SC SF

Rangers (n) 8 Apr 00 SC SF

St Mirren (a) 18 Dec 99

St Mirren (a) 18 Dec 99

St Mirren (a) 7 Aug 99

St Mirren (a) 7 Aug 99

St Mirren (h) 22 Apr 00

St Mirren (h) 22 Apr 00

St Mirren (h) 23 Oct 99

St Mirren (h) 23 Oct 99

Wrexham (h) 31 Jul 99

Wrexham (h) 31 Jul 99