Dundee United v Ross County, 18 August 1999
| Score | 3-1 to Dundee United |
| Referee | Kenny Clark |
| Competition | Scottish League Cup 2nd round |
| Venue | Tannadice, Dundee |
| Attendance | 4,673 |
3 Dundee United
Goals:
| Joaquim Ferraz | 27 |
|
|
| Steven Thompson | 113 |
|
|
| Steven Thompson | 119 |
|
Starting lineup:
Goalkeeper
Alan Combe
Defender
David Partridge
Defender
David Worrell
Defender/Centre back
Jason De Vos
Defender/Midfielder
Jim Paterson
Midfielder
Hugh Davidson
Midfielder
David Hannah
Forward
Billy Dodds
Substitutions:
| Craig Easton for David Worrell | 64 |
| Alex Mathie for Hugh Davidson | 76 |
| Steven Thompson for Joaquim Ferraz | 97 |
Cards:
| Jim Paterson | Y |
1 Ross County
Goals:
| Franck Escalon | 41 |
|
Starting lineup:
Nicky Walker
Goalkeeper
Brian Irvine
Defender
Ian Maxwell
Defender
Craig Tully
Defender
Roy McBain
Defender/Midfielder
Steven Ferguson
Midfielder
Kenny Gilbert
Midfielder
John McGlashan
Midfielder
Franck Escalon
Forward
Kevin Finlayson
Forward
George Shaw
Forward
Substitutions:
| Michael Geraghty for Kevin Finlayson | 55 |
| John Fraser for Franck Escalon | 112 |
| Garry Wood for Steven Ferguson | 115 |
Cards:
| Steven Ferguson | Y | |
| Garry Wood | Y |