Dundee v Dundee United, 17 October 1999
| Score | 2-0 to Dundee United |
| Referee | John Rowbotham |
| Competition | Scottish Premier League |
| Venue | Dens Park, Dundee |
| Attendance | 9,484 |
0 Dundee
Goals:
Starting lineup:
Goalkeeper
Rab Douglas
Defender
Lee Maddison
Defender
Steven Tweed
Defender
Lee Wilkie
Defender/Left back
Lee Sharp
Midfielder
Steven Boyack
Midfielder
Shaun McSkimming
Midfielder
Gavin Rae
Forward
Eddie Annand
Forward
Willie Falconer
Forward
James Grady
Substitutions:
| Roberto Matute for Eddie Annand | 59 |
| Hugh Robertson for Lee Maddison | 79 |
| Tommy Coyne for James Grady | 79 |
Cards:
| Gavin Rae | Y |
2 Dundee United
Goals:
| Billy Dodds | 14 |
|
|
| Steven Thompson | 51 |
|
Starting lineup:
Alan Combe
Goalkeeper
David Partridge
Defender
Jason De Vos
Defender/Centre back
Scott McCulloch
Defender/Centre back
Hugh Davidson
Midfielder
Craig Easton
Midfielder
David Hannah
Midfielder
Jan Talesnikov
Midfielder
Billy Dodds
Forward
Steven Thompson
Forward
Substitutions:
| Magnus Skoldmark for Hugh Davidson | 89 |
Cards:
| Craig Easton | Y |