Macclesfield Town v Middlesbrough, 26 September 2000
| Score | 3-1 to Middlesbrough |
| Referee | Alan Wiley |
| Competition | League Cup 2nd round 2nd leg |
| Venue | Moss Rose |
| Attendance | 3,153 |
View Macclesfield Town v Middlesbrough head to head
Goals:
| Ben Sedgemore | penalty | 38 |
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Starting lineup:
Goalkeeper
Tony Bullock
Defender/Right back
George Abbey
Defender
Rae Ingram
Defender/Centre back
Darren Tinson
Defender/Left back
Danny Adams
Midfielder
Kevin Keen
Midfielder
Karl Munroe
Midfielder
Ben Sedgemore
Midfielder
Gary Twynham
Midfielder
Steve Wood
Forward
Richie Barker
Substitutions:
| Damien Whitehead for Steve Wood | 58 |
| John Askey for Ben Sedgemore | 68 |
| Mike Bamber for Steve Wood | 77 |
Cards:
| Richie Barker | 27 | Y |
| Gary Twynham | 38 | Y |
Goals:
| Hamilton Ricard | 18 |
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| Hamilton Ricard | 51 |
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| Hamilton Ricard | 53 |
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Starting lineup:
Mark Crossley
Goalkeeper
Gianluca Festa
Defender
Curtis Fleming
Defender
Colin Cooper
Defender/Centre back
Dean Gordon
Defender/Left back
Paul Ince
Midfielder
Mark Summerbell
Midfielder
Andy Campbell
Forward
Brian Deane
Forward
Hamilton Ricard
Forward
Noel Whelan
Forward
Substitutions:
| Carlos Marinelli for Andy Campbell | 56 |
| Phil Stamp for Brian Deane | 75 |
Cards:
| Mark Summerbell | 27 | Y |
| Hamilton Ricard | 28 | Y |
| Paul Ince | 78 | Y |