Clyde v Hibernian, 17 August 1999
| Score | 2-2 |
| Referee | Douglas McDonald |
| Competition | Scottish League Cup 2nd round |
| Venue | Broadwood Stadium, Cumbernauld |
| Attendance | 2,008 |
After extra time. Hibernian won 5-4 on penalties.
2 Clyde
Goals:
| Thomas Woods | 14 |
|
|
| Brian Carrigan | 30 |
|
Starting lineup:
Goalkeeper
David Wylie
Defender
Craig Cranmer
Defender
Pat Keogh
Defender
Mark McLaughlin
Defender
Darren Murray
Defender
Bryan Smith
Midfielder
Ritchie McCusker
Forward
Brian Carrigan
Forward
Stevie Convery
Forward
Thomas Woods
Substitutions:
| Stephen Craib for Ritchie McCusker | 48 |
| Jack Ross for Thomas Woods | 68 |
| Martin McLauchlan for Mark McLaughlin | 79 |
Cards:
| Ian Spittal | Y |
2 Hibernian
Goals:
| Pat McGinlay | 9 |
|
|
| Paul Hartley | 16 |
|
Starting lineup:
Nick Colgan
Goalkeeper
Alex Marinkov
Defender/Centre back
Paul Lovering
Full back
Paul Hartley
Midfielder
Stuart Lovell
Midfielder
Pat McGinlay
Midfielder
Justin Skinner
Midfielder
Tom Smith
Midfielder
Stevie Crawford
Forward
John Hughes
Forward
Dirk Lehmann
Forward
Substitutions:
| Matthias Jack for Alex Marinkov | 46 |
| Russell Latapy for Dirk Lehmann | 59 |
| Kenny Miller for Paul Hartley | 104 |
Cards:
| John Hughes | Y | |
| Paul Lovering | Y | |
| Paul Hartley | Y |