Dundee v Montrose, 23 August 2000
| Score | 3-0 to Dundee |
| Referee | Alan Freeland |
| Competition | Scottish League Cup 2nd round |
| Venue | Dens Park, Dundee |
| Attendance | 2,635 |
3 Dundee
Goals:
| Lee Wilkie | 5 |
|
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| Fabian Caballero | 56 |
|
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| Fabian Caballero | 66 |
|
Starting lineup:
Goalkeeper
Rab Douglas
Defender
Barry Smith
Defender
Steven Tweed
Defender
Lee Wilkie
Defender/Left back
Marcello Marrocco
Midfielder
Patricio Billio
Midfielder
Giorgi Nemsadze
Midfielder
Gavin Rae
Forward
Fabian Caballero
Forward
Willie Falconer
Forward
Michael Yates
Substitutions:
| Chris Coyne for Steven Tweed | 21 |
| Shaun McSkimming for Marcello Marrocco | 46 |
| Juan Sara for Fabian Caballero | 67 |
Cards:
| Chris Coyne | 73 | Y |
0 Montrose
Goals:
Starting lineup:
Gary McGlynn
Goalkeeper
Scott Sneddon
Defender
Mark Craib
Centre back
Stuart Ferguson
Full back
Craig Mailer
Full back
John Young
Full back
Tommy Harrison
Midfielder
Steven Marwick
Midfielder
Stuart Robertson
Midfielder
James McKellar
Forward
Mike McKenzie
Forward
Substitutions:
| Jerry O'Driscoll for James McKellar | 65 |
| Paul McIlravey for Mike McKenzie | 65 |
| Ross McWilliam for Stuart Robertson | 74 |
Cards:
| Stuart Ferguson | 81 | Y |