Leyton Orient 5 Middlesbrough 0
Outcome: Lost
Date: 10/31/1959
Manager: Bob Dennison
Attendance: 15600
Competition: DivisionTwo
Played at: Brisbane Road
Goals:
| Goals | Time | Assists |
Team
| Player | Yellow | Red | Subbed |
| Eddie Holliday | |||
| Bill Harris | |||
| Alan Peacock | |||
| Billy Day | |||
| Brian Clough | |||
| Willie Fernie | |||
| Ray Yeoman | |||
| Mick McNeil | |||
| Ray Bilcliff | |||
| Brian Phillips | |||
| Peter Taylor |
Subs
| Player | Yellow | Red | Subbed |