Leyton Orient 2 Middlesbrough 4
Outcome: Won
Date: 4/4/1959
Manager: Bob Dennison
Attendance: 20683
Competition: DivisionTwo
Played at: Ayresome Park
Goals:
| Goals | Time | Assists | |
| Brian Clough | |||
| Bill Harris | |||
| Alan Peacock | |||
| Alan Peacock | |||
Team
| Player | Yellow | Red | Subbed |
| Eddie Holliday | |||
| Bill Harris | |||
| Alan Peacock | |||
| Brian Clough | |||
| Willie Fernie | |||
| Ray Yeoman | |||
| Ron Burbeck | |||
| Derek Stonehouse | |||
| Ray Barnard | |||
| Brian Phillips | |||
| Peter Taylor |
Subs
| Player | Yellow | Red | Subbed |