Gillingham v Bolton Wanderers, 14 September 1999
| Score | 4-1 to Bolton Wanderers |
| Competition | League Cup 2nd round 1st leg |
| Venue | Priestfield Stadium |
| Attendance | 4,996 |
View Gillingham v Bolton Wanderers head to head
Goals:
| Andy Hessenthaler | 45 |
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Starting lineup:
Goalkeeper
Tony Williams
Defender/Centre back
Barry Ashby
Defender/Centre back
Adrian Pennock
Defender/Midfielder
Brian McGlinchey
Midfielder
Andy Hessenthaler
Midfielder
Manny Omoyinmi
Midfielder
Mark Saunders
Midfielder
Paul Smith
Midfielder
Nicky Southall
Forward
John Hodge
Forward
Andy Thomson
Substitutions:
| Barry Miller for Mark Saunders | 0 |
| Nyron Nosworthy for Manny Omoyinmi | 0 |
| James Pinnock for John Hodge | 0 |
On the bench:
Defender/Full back
Barry Miller
Defender/Midfielder
Nyron Nosworthy
Forward
James Pinnock
Goals:
| Neil Cox | 17 |
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| Eidur Gudjohnsen | 44 |
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| Eidur Gudjohnsen | 58 |
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| Gudni Bergsson | 64 |
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Starting lineup:
Steve Banks
Goalkeeper
Gudni Bergsson
Defender
Neil Cox
Defender
Mike Whitlow
Defender
Robbie Elliott
Defender/Midfielder
Andy Todd
Defender/Midfielder
Per Frandsen
Midfielder
Ricardo Gardner
Midfielder
Michael Johansen
Midfielder
Eidur Gudjohnsen
Forward
Bob Taylor
Forward
Substitutions:
| Bo Hansen for Mike Whitlow | 0 |
| Paul Warhurst for Gudni Bergsson | 0 |