East Fife v Heart of Midlothian, 12 October 1999
| Score | 2-0 to Heart of Midlothian |
| Referee | Kenny Clark |
| Competition | Scottish League Cup 3rd round |
| Venue | Stark's Park, Kirkcaldy |
| Attendance | 3,337 |
0 East Fife
Goals:
Starting lineup:
Goalkeeper
Willie McCulloch
Defender
Damiano Agostini
Defender
Gordon Forrest
Defender
Graeme Love
Defender
Rab Shannon
Centre back
Billy Herd
Midfielder
John Cusick
Midfielder
Raymond Logan
Midfielder
Stuart MacKay
Midfielder
Graham Robertson
Forward
Barrie Moffat
Substitutions:
| Steven Ramsay for John Cusick | 71 |
| Stephen Kirk for Barrie Moffat | 75 |
| Ben Honeyman for Raymond Logan | 84 |
Cards:
| Graeme Love | Y |
2 Heart of Midlothian
Goals:
| Colin Cameron | penalty | 41 |
|
| Derek Holmes | 89 |
|
Starting lineup:
Gilles Rousset
Goalkeeper
Rob McKinnon
Defender
Steven Pressley
Defender
Paul Ritchie
Defender
Colin Cameron
Midfielder
Thomas Flogel
Midfielder
Stephen Fulton
Midfielder
Scott Severin
Midfielder
Darren Jackson
Forward
Fabien LeClercq
Forward
Gary McSwegan
Forward
Substitutions:
| Derek Holmes for Stephen Fulton | 75 |
| Gary Wales for Gary McSwegan | 89 |
Cards:
| Fabien LeClercq | Y | |
| Steven Pressley | Y |