Ayr United v Dundee, 15 February 2000
| Score | 1-1 |
| Referee | Jim Herald |
| Competition | Scottish FA Cup 3rd round replay |
| Venue | Somerset Park, Ayr |
| Attendance | 3,029 |
After extra time. Ayr United won 7-6 on penalties.
1 Ayr United
Goals:
| Neil Duffy | 104 |
|
Starting lineup:
Goalkeeper
Craig Nelson
Defender
David Craig
Defender
Lyndon McMillan
Defender
Paul Shepherd
Defender/Midfielder
Neil Duffy
Full back
John Robertson
Midfielder
Neil Scally
Midfielder
Marvyn Wilson
Forward
Glynn Hurst
Forward
Neil Tarrant
Forward
Gary Teale
Substitutions:
| Michael Reynolds for Neil Tarrant | 70 |
| Mark Crilly for Neil Scally | 85 |
| Roddy Grant for Lyndon McMillan | 101 |
Cards:
| Neil Scally | Y |
1 Dundee
Goals:
| Gavin Rae | 91 |
|
Starting lineup:
Jamie Langfield
Goalkeeper
Robert Raeside
Defender
Barry Smith
Defender
Steven Tweed
Defender
Lee Wilkie
Defender
Hugh Robertson
Defender/Left back
Steven Boyack
Midfielder
Shaun McSkimming
Midfielder
Gavin Rae
Midfielder
Graham Bayne
Forward
Willie Falconer
Forward
Substitutions:
| Nicky Banger for Steven Boyack | 62 |
| James Grady for Graham Bayne | 79 |
| Lee Sharp for Shaun McSkimming | 119 |
Cards:
| Gavin Rae | Y |