Bolton Wanderers v Gillingham, 21 September 1999
| Score | 2-0 to Bolton Wanderers |
| Competition | League Cup 2nd round 2nd leg |
| Venue | Reebok Stadium |
| Attendance | 3,673 |
View Bolton Wanderers v Gillingham head to head
Bolton Wanderers won 6-1 on aggregate.
Goals:
| Bo Hansen | 4 |
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| Dean Holdsworth | 7 |
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Starting lineup:
Goalkeeper
Steve Banks
Defender
Gudni Bergsson
Defender/Centre back
Greg Strong
Defender/Midfielder
Hasney Aljofree
Defender/Midfielder
Andy Todd
Defender/Midfielder/Forward
Paul Warhurst
Defender/Left back
Jimmy Phillips
Midfielder
Ricardo Gardner
Midfielder
Michael Johansen
Forward
Bo Hansen
Forward
Dean Holdsworth
Substitutions:
| Mark Fish for Gudni Bergsson | 0 |
| Lee Potter for Hasney Aljofree | 0 |
| Luke Staton for Ricardo Gardner | 0 |
Goals:
Starting lineup:
Tony Williams
Goalkeeper
Barry Ashby
Defender/Centre back
Guy Butters
Defender/Centre back
Adrian Pennock
Defender/Centre back
Barry Miller
Defender/Full back
Brian McGlinchey
Defender/Midfielder
Andy Hessenthaler
Midfielder
Junior Lewis
Midfielder
Manny Omoyinmi
Midfielder
Paul Smith
Midfielder
Andy Thomson
Forward
Substitutions:
| Mick Galloway for Andy Hessenthaler | 0 |
| Nyron Nosworthy for Manny Omoyinmi | 0 |