Alloa Athletic v Dundee, 12 October 1999
| Score | 3-1 to Dundee |
| Referee | John Underhill |
| Competition | Scottish League Cup 3rd round |
| Venue | Recreation Park, Alloa |
| Attendance | 1,344 |
1 Alloa Athletic
Goals:
| Ian Cameron | 1 |
|
Starting lineup:
Goalkeeper
Mark Cairns
Defender
David Beaton
Defender
James Boyle
Defender
Craig Valentine
Midfielder
Ian Cameron
Midfielder
Martin Christie
Midfielder
Derek Clark
Midfielder
Gary Clark
Midfielder
William Irvine
Midfielder
Mark Wilson
Forward
Scott Bannerman
Substitutions:
| David Menelaws for Scott Bannerman | 46 |
| Ray Sharp for Gary Clark | 63 |
| Mark Donaghy for Mark Wilson | 63 |
Cards:
| Derek Clark | Y |
On the bench:
3 Dundee
Goals:
| Willie Falconer | 20 |
|
|
| James Grady | 40 |
|
|
| Willie Falconer | 52 |
|
Starting lineup:
Rab Douglas
Goalkeeper
Lee Maddison
Defender
Willie Miller
Defender
Barry Smith
Defender
Steven Tweed
Defender
Steven Boyack
Midfielder
Shaun McSkimming
Midfielder
Gavin Rae
Midfielder
Eddie Annand
Forward
Willie Falconer
Forward
James Grady
Forward
Substitutions:
| Hugh Robertson for Gavin Rae | 80 |
Cards:
On the bench:
Defender/Left back
Hugh Robertson