Chesterfield 2 Middlesbrough 1
Outcome: Lost
Date: 12/2/1986
Manager: Bruce Rioch
Attendance: 1764
Competition: FreightRoverTrophy SecondRound
Played at: Saltergate
Goals:
| Goals | Time | Assists | |
| Archie Stephens | |||
Team
| Player | Yellow | Red | Subbed |
| Bernie Slaven | |||
| Stuart Ripley | |||
| Archie Stephens | |||
| Gary Hamilton | |||
| Gary Gill | |||
| Colin Cooper | |||
| Gary Pallister | |||
| Gary Parkinson | |||
| Tony Mowbray | |||
| Brian Laws | |||
| Stephen Pears |
Subs
| Player | Yellow | Red | Subbed |