Middlesbrough v Macclesfield Town, 19 September 2000
| Score | 2-1 to Middlesbrough |
| Referee | Matt Messias |
| Competition | League Cup 2nd round 1st leg |
| Venue | Riverside Stadium |
| Attendance | 5,144 |
View Middlesbrough v Macclesfield Town head to head
Goals:
| Noel Whelan | 87 |
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| Mark Summerbell | 90 |
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Starting lineup:
Goalkeeper
Chris Bennion
Defender
Gianluca Festa
Defender/Centre back
Colin Cooper
Defender/Centre back
Jason Gavin
Defender/Midfielder
Stuart Parnaby
Defender/Left back
Dean Gordon
Midfielder
Paul Ince
Midfielder
Mark Summerbell
Forward
Alun Armstrong
Forward
Hamilton Ricard
Forward
Noel Whelan
Substitutions:
| Alen Boksic for Hamilton Ricard | 65 |
| Joseph-Desire Job for Dean Gordon | 68 |
| Keith O'Neill for Alun Armstrong | 84 |
Goals:
| Richie Barker | 59 |
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Starting lineup:
Tony Bullock
Goalkeeper
George Abbey
Defender/Right back
Steve Hitchen
Defender/Right back
Rae Ingram
Defender
Darren Tinson
Defender/Centre back
Kieron Durkan
Midfielder
Karl Munroe
Midfielder
Ben Sedgemore
Midfielder
Steve Wood
Midfielder
John Askey
Midfielder/Forward
Richie Barker
Forward
Substitutions:
| Lee Glover for Steve Hitchen | 74 |
| Kevin Keen for John Askey | 88 |