Portsmouth v Middlesbrough, 22 November 1969
| Score | 3-2 to Middlesbrough |
| Competition | League Division Two |
| Venue | Fratton Park |
| Attendance | 15,621 |
View Portsmouth v Middlesbrough head to head
Goals:
| John Hickton |
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| Hugh McIlmoyle |
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| Joe Laidlaw |
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Starting lineup:
Willie Whigham
Goalkeeper
Micky Allen
Defender
Bill Gates
Defender
Gordon Jones
Defender
Alex Smith
Defender
Frank Spraggon
Defender
Derrick Downing
Midfielder
Joe Laidlaw
Midfielder
George Smith
Midfielder
John Hickton
Forward
Hugh McIlmoyle
Forward
Substitutions:
| Eric McMordie for Micky Allen |
On the bench:
Midfielder
Eric McMordie