Chester v Middlesbrough, 26 November 1966
| Score | 5-2 to Middlesbrough |
| Competition | FA Cup 1st round |
| Attendance | 7,607 |
View Chester v Middlesbrough head to head
Goals:
| John Hickton |
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| John O'Rourke |
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| John O'Rourke |
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| John O'Rourke |
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| Derrick Downing |
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Starting lineup:
Willie Whigham
Goalkeeper
Neville Chapman
Right back
Geoff Butler
Defender
Billy Horner
Defender
Gordon Jones
Defender
Dickie Rooks
Centre half
Dave Chadwick
Midfielder
Derrick Downing
Midfielder
John O'Rourke
Centre forward
John Hickton
Forward
Arthur Horsfield
Forward
Substitutions:
| Frank Spraggon for John O'Rourke |
On the bench:
Defender
Frank Spraggon