Rangers v Dunfermline Athletic, 12 October 1999
| Score | 1-0 to Rangers |
| Referee | Michael McCurry |
| Competition | Scottish League Cup 3rd round |
| Venue | Ibrox Stadium, Glasgow |
| Attendance | 30,024 |
1 Rangers
Goals:
| Rodney Wallace | 24 |
|
Starting lineup:
Goalkeeper
Mark Brown
Defender
Dariusz Adamczuk
Defender
Craig Moore
Defender
Tony Vidmar
Defender/Centre back
Lorenzo Amoruso
Midfielder
Jorg Albertz
Midfielder
Andrei Kanchelskis
Midfielder
Derek McInnes
Forward
Gabriel Amato
Forward
Jonatan Johansson
Forward
Rodney Wallace
Substitutions:
| Michael Mols for Jonatan Johansson | 64 |
| Sergio Porrini for Gabriel Amato | 80 |
Cards:
| Derek McInnes | Y |
0 Dunfermline Athletic
Goals:
Starting lineup:
Ian Westwater
Goalkeeper
John Potter
Defender
Brian Reid
Defender/Centre back
Jason Dair
Midfielder
Jamie Dolan
Midfielder
Hamish French
Midfielder
Scott M Thomson
Midfielder
Owen Coyle
Forward
David Graham
Forward
Stewart Petrie
Forward
Andrew Smith
Forward
Substitutions:
| Eddie May for Andrew Smith | 71 |
| Chris McGroarty for Jamie Dolan | 77 |
Cards:
| Owen Coyle | Y | |
| Jamie Dolan | Y |