The 1999–2000 Ayr United season was the 103rd season of competitive football in Scotland and the 85th season of competitive football and the 89th season in the clubs history.
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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.
| Date | Opponents | H/A | Competition | Score - Ayr First | Comments | Att |
| |
| 19/7/99 | Oxford United | H | Friendly | 1-0 | Yes | |||
| 22/07/1999 | Fraserburgh | A | Friendly | 6-1 | 1999 Highland Tour | No Issue | ||
| 24/07/1999 | Huntly | A | Friendly | 2-0 | 1999 Highland Tour | No Issue | ||
| 26/07/1999 | Keith | A | Friendly | 7-0 | 1999 Highland Tour | Yes | ||
| 28/07/1999 | Peterhead | A | Friendly | 3-2 | 1999 Highland Tour | No Issue | ||
| 31/7/99 | Wrexham | H | Friendly | 3-0 | Yes | |||
| 7/8/99 | St. Mirren | A | 1st Division | 1-1 | Yes | |||
| 10/8/99 | Raith Rovers | H | Challenge Cup – 1st Rnd | 0-1 | Yes | |||
| 14/8/99 | Livingston | H | 1st Division | 1-2 | Yes | |||
| 17/8/99 | Hamilton Academical | H | Scottish League Cup - 2nd Round | 2-1 | Yes | |||
| 21/8/99 | Falkirk | A | 1st Division | 1-2 | Yes | |||
| 28/8/99 | Inverness C T | H | 1st Division | 1-0 | 2,157 | Yes | ||
| 4/9/99 | Raith Rovers | A | 1st Division | 1-5 | Yes | |||
| 11/9/99 | Airdrieonians 1878 | H | 1st Division | 2-0 | Yes | |||
| 18/9/99 | Clydebank 1965 | A | 1st Division | 2-0 | Yes | |||
| 25/9/99 | Dunfermline Athletic | H | 1st Division | 1-2 | Yes | |||
| 2/10/99 | Morton | H | 1st Division | 3-0 | Yes | |||
| 7/10/99 | Dundee United | H | Friendly | 3-2 | Yes | |||
| 13/10/1999 | Celtic | H | Scottish League Cup - 3rd Rnd | 0-4 | Yes | |||
| 16/10/99 | Livingston | A | 1st Division | 1-4 | Yes | |||
| 23/10/99 | St. Mirren | H | 1st Division | 0-3 | Yes | |||
| 30/10/99 | Airdrieonians 1878 | A | 1st Division | 1-2 | Yes | |||
| 6/11/99 | Clydebank 1965 | H | 1st Division | 0-0 | Yes | |||
| 14/11/99 | Raith Rovers | H | 1st Division | 0-1 | Yes | |||
| 27/11/99 | Morton | A | 1st Division | 0-0 | Yes | |||
| 30/11/99 | Inverness
C T |
A | 1st Division | 1-1 | 1,050 | Yes | ||
| 4/12/99 | Dunfermline Athletic | H | 1st Division | 0-3 | Yes | |||
| 11/12/99 | Falkirk | H | 1st Division | 1-1 | Yes | |||
| 18/12/99 | St. Mirren | A | 1st Division | 2-1 | Yes | |||
| 27/12/99 | Airdrieonians 1878 | H | 1st Division | 5-0 | Yes | |||
| 3/1/00 | Clydebank 1965 | A | 1st Division | 2-0 | No Issue | |||
| 8/1/00 | Raith Rovers | A | 1st Division | 0-2 | Yes | |||
| 22/1/00 | Dunfermline
Athletic |
A | 1st Division | 0-2 | Yes | |||
| 29/1/00 | Dundee | A | Scottish Cup - 3rd Rnd | 0-0 | Yes | |||
| 5/2/00 | Morton | H | 1st Division | 3-2 | Yes | |||
| 12/2/00 | Falkirk | A | 1st Division | 0-1 | Yes | |||
| 15/2/00 | Dundee | H | Scottish Cup - 3rd Rnd Replay | 1-1 AET Ayr win 7-6 on penalties | Programme from match of 8th February 2000 used – no insert | No Issue | ||
| 26/2/00 | Motherwell | A | Scottish Cup - 4th Rnd | 4-3 | Yes | |||
| 29/2/00 | Livingston | H | 1st Division | 0-1 | Yes | |||
| 4/3/00 | Airdrieonians 1878 | A | 1st Division | 0-0 | Yes | |||
| 7/3/00 | Inverness C T | H | 1st Division | 1-3 | 1,274 | Yes | ||
| 11/3/00 | Partick Thistle | H | Scottish Cup - 5th Rnd | 2-0 | Yes | |||
| 18/3/00 | Clydebank 1965 | H | 1st Division | 4-0 | Yes | |||
| 25/3/00 | Inverness C T | A | 1st Division | 1-1 | 1,790 | Yes | ||
| 1/4/00 | Raith Rovers | H | 1st Division | 0-1 | Yes | |||
| 8/1/00 | Rangers | N | Scottish Cup - Semi Final | 0-7 | Yes | |||
| 11/4/00 | Dunfermline
Athletic |
H | 1st Division | 0-2 | Yes | |||
| 15/4/00 | Morton | A | 1st Division | 2-1 | Yes | |||
| 22/4/00 | St. Mirren | H | 1st Division | 1-2 | Yes | |||
| 29/4/00 | Livingston | A | 1st Division | 1-3 | Yes | |||
| 6/5/00 | Falkirk | H | 1st Division | 3-3 | Yes |