Queen of the South v Heart of Midlothian, 18 August 1999
| Score | 3-1 to Heart of Midlothian |
| Referee | Hugh Dallas |
| Competition | Scottish League Cup 2nd round |
| Venue | Palmerston Park, Dumfries |
| Attendance | 4,633 |
1 Queen of the South
Goals:
| Steven Leslie | 14 |
|
Starting lineup:
Goalkeeper
John Hillcoat
Defender
Andrew Aitken
Defender
David Lilley
Defender
George Rowe
Midfielder
Paul Harvey
Forward
Charlie Adams
Forward
Bryan Caldwell
Forward
Stevie Mallan
Substitutions:
| Lee Bailey for Charlie Adams | 75 |
| Billy Findlay for Paul Harvey | 76 |
Cards:
| David Lilley | Y |
3 Heart of Midlothian
Goals:
| Darren Jackson | 46 |
|
|
| Scott Severin | 70 |
|
|
| Darren Jackson | 85 |
|
Starting lineup:
Gilles Rousset
Goalkeeper
Gary Naysmith
Defender
Steven Pressley
Defender
Paul Ritchie
Defender
Kevin James
Centre back
Colin Cameron
Midfielder
Gary Locke
Midfielder
Lee Makel
Midfielder
Scott Severin
Midfielder
Carricondo Perez Juanjo
Forward
Gary McSwegan
Forward
Substitutions:
| Darren Jackson for Carricondo Perez Juanjo | 46 |
| Stephen Fulton for Lee Makel | 77 |
| Jose Quitongo for Gary McSwegan | 89 |
Cards:
| Lee Makel | Y | |
| Colin Cameron | Y |