Portsmouth 6 Middlesbrough 3
Outcome: Lost
Date: 12/19/1959
Manager: Bob Dennison
Attendance: 9912
Competition: DivisionTwo
Played at: Fratton Park
Goals:
| Goals | Time | Assists | |
| Brian Clough | |||
| Bill Harris | |||
| Billy Day | |||
Team
| Player | Yellow | Red | Subbed |
| Eddie Holliday | |||
| Bill Harris | |||
| Alan Peacock | |||
| Billy Day | |||
| Brian Clough | |||
| Willie Fernie | |||
| Ray Yeoman | |||
| Mick McNeil | |||
| Ken Thomson | |||
| Ray Bilcliff | |||
| Peter Taylor |
Subs
| Player | Yellow | Red | Subbed |