| Date | 14 September 1999 |
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| Competition | Scottish Challenge Cup |
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| Fixture/Score | Ross County 1:2 Alloa Athletic |
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| Venue | Victoria Park |
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| Attendance | 1,202 |
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| Referee | George Simpson |
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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: Martin Canning, 3: Ian Maxwell, 4: Brian Irvine, 5: John Fraser 1, 6: Franck Escalon, 7: Paul Kinnaird, 8: Kenneth Gilbert 1, 9: Steven Ferguson 1, 10: Garry Wood, 11: George Shaw 1 1 |
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| Bench | 0: Roy McBain, 0: David Ross, 0: Kevin Finlayson |
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| Alloa Athletic |
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| Manager | Terry Christie |
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| Starting 11 | Mark Cairns, Mark Nelson, Craig Valentine, Ray Sharp, Davie Beaton, Derek Clark 1, Mark Donaghy 1 1, Max Christie, Gregor McKechnie, Martin Cameron, David Menelows |
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| Bench | Jimmy Boyle, Gary Clark, William Irvine 1 |
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