Dundee United v Motherwell, 01 December 1999
| Score | 3-2 to Dundee United |
| Referee | Douglas McDonald |
| Competition | Scottish League Cup Quarter-final |
| Venue | Tannadice, Dundee |
| Attendance | 5,086 |
3 Dundee United
Goals:
| Billy Dodds | penalty | 26 |
|
| Craig Easton | 42 |
|
|
| Steven Thompson | 84 |
|
Starting lineup:
Goalkeeper
Alan Combe
Defender
David Partridge
Defender
David Worrell
Defender/Centre back
Jason De Vos
Midfielder
Hugh Davidson
Midfielder
Craig Easton
Midfielder
David Hannah
Midfielder
Jan Talesnikov
Forward
Billy Dodds
Forward
Steven Thompson
Substitutions:
| Joaquim Ferraz for Hugh Davidson | 76 |
| Maurice Malpas for Steven Thompson | 88 |
Cards:
| David Hannah | 88 | R |
2 Motherwell
Goals:
| Derek Townsley | 53 |
|
|
| Shaun Teale | penalty | 86 |
|
Starting lineup:
Stephen Woods
Goalkeeper
Ged Brannan
Defender
Michel Doesburg
Defender
Stephen McMillan
Defender
Benito Kemble
Defender/Centre back
Shaun Teale
Defender/Centre back
Derek Townsley
Midfielder
Kevin Twaddle
Midfielder
Simo Valakari
Midfielder
Don Goodman
Forward
Steve Halliday
Forward
Substitutions:
| Pat Nevin for Kevin Twaddle | 32 |
| John Spencer for Steve Halliday | 53 |