Raith Rovers v Motherwell, 18 August 1999
| Score | 2-2 |
| Referee | Ian Fyfe |
| Competition | Scottish League Cup 2nd round |
| Venue | Stark's Park, Kirkcaldy |
| Attendance | 2,393 |
After extra time. Motherwell won 5-4 on penalties.
2 Raith Rovers
Goals:
| Alex Burns | 75 |
|
|
| Craig Dargo | 85 |
|
Starting lineup:
Goalkeeper
Guido Van De Kamp
Defender
Paul Browne
Defender
Craig McEwan
Defender/Centre back
Marvin Andrews
Full back
Laurie Ellis
Midfielder
Kenneth Black
Midfielder
Jay Stein
Midfielder
Steve Tosh
Forward
Alex Burns
Forward
Andy Clark
Forward
Paul Tosh
Substitutions:
| Craig Dargo for Andy Clark | 60 |
| Paul Agnew for Paul Tosh | 60 |
| Steven Hamilton for Kenneth Black | 71 |
Cards:
| Alex Burns | Y | |
| Kenneth Black | Y | |
| Paul Tosh | Y | |
| Paul Browne | Y |
2 Motherwell
Goals:
| Paul Browne | own goal | 5 |
|
| Steve Halliday | 74 |
|
Starting lineup:
Andy Goram
Goalkeeper
Ged Brannan
Defender
Michel Doesburg
Defender
Jamie McGowan
Defender
Stephen McMillan
Defender
Tony Thomas
Defender
Derek Townsley
Midfielder
Pat Nevin
Midfielder/Forward
Derek Adams
Forward
Don Goodman
Forward
John Spencer
Forward
Substitutions:
| Steve Halliday for Derek Townsley | 60 |
| Stephen Craigan for Ged Brannan | 92 |
| Stephen Nicholas for Pat Nevin | 116 |
Cards:
| Jamie McGowan | Y | |
| Michel Doesburg | Y |