| Date | 18 August 1999 |
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| Competition | Scottish League Cup |
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| Fixture/Score | Dundee United 3:1 Ross County |
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| Venue | Tannadice Park |
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| Attendance | 4,682 |
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| Referee | Kenny Clark |
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| Comments | Loss After Extra Time |
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| Ross County |
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| Manager | Neale Cooper |
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| Starting 11 | 1: Joseph Walker, 2: Craig Tully, 3: Ian Maxwell, 4: Brian Irvine, 5: Steven Ferguson 1, 6: Roy McBain, 7: Franck Escalon 1, 8: John McGlashan, 9: Kenneth Gilbert, 10: George Shaw, 11: Kevin Finlayson |
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| Bench | 0: John Fraser, 0: Michael Geraghty, 0: Garry Wood 1 |
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| Dundee United |
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| Manager | Paul Sturrock |
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| Starting 11 | Alan Combe, David Partridge, Bernard Pascual, Magnus Skoldmark, Jason De Vos, David Worrell, Hugh Davidson, David Hannah, Darren Patterson 1, Billy Dodds, Joaquim Ferraz 1 |
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| Bench | Craig Easton, Alex Mathie, Steven Thompson 2 |
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