Dundee v Dumbarton, 17 August 1999
| Score | 4-0 to Dundee |
| Referee | Tom Brown |
| Competition | Scottish League Cup 2nd round |
| Venue | Dens Park, Dundee |
| Attendance | 2,675 |
4 Dundee
Goals:
| Steven Boyack | 17 |
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| Willie Falconer | 31 |
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| Willie Falconer | 35 |
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| Steven Boyack | 90 |
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Starting lineup:
Goalkeeper
Rab Douglas
Defender
Willie Miller
Defender
Barry Smith
Defender
Steven Tweed
Defender/Left back
Hugh Robertson
Defender/Left back
Lee Sharp
Midfielder
Steven Boyack
Midfielder
Gavin Rae
Forward
Eddie Annand
Forward
Willie Falconer
Forward
Michael Yates
Substitutions:
| Frank Van Eijs for Willie Miller | 46 |
| Shaun McSkimming for Hugh Robertson | 72 |
| Robert Raeside for Michael Yates | 78 |
0 Dumbarton
Goals:
Starting lineup:
Kenneth Meechan
Goalkeeper
Craig Brittain
Defender
Jamie Bruce
Defender
Michael Dickie
Defender
Alex Grace
Midfielder
Stephen Jack
Midfielder
Toby King
Midfielder
Billy Melvin
Midfielder
Andy Brown
Forward
Patrick Flannery
Forward
Joseph Robertson
Forward
Substitutions:
| Scott McHarg for Billy Melvin | 56 |
| Martin Melvin for Joseph Robertson | 56 |
| John Dillon for Alex Grace | 64 |