Leyton Orient 2 Middlesbrough 1
Outcome: Lost
Date: 2/9/1957
Manager: Bob Dennison
Attendance: 27315
Competition: DivisionTwo
Played at: Ayresome Park
Goals:
| Goals | Time | Assists | |
| Brian Clough | |||
Team
| Player | Yellow | Red | Subbed |
| Bill Harris | |||
| Billy Day | |||
| Derek McLean | |||
| Brian Clough | |||
| Ronnie Dicks | |||
| Joe Scott | |||
| Ron Burbeck | |||
| Derek Stonehouse | |||
| Ray Barnard | |||
| Dick Robinson | |||
| Peter Taylor |
Subs
| Player | Yellow | Red | Subbed |