York City 2 Middlesbrough 1
Outcome: Lost
Date: 8/29/1966
Manager: Stan Anderson
Attendance: 4790
Competition: LeagueCup FirstRoundReplay
Played at: Bootham Crescent
Goals:
| Goals | Time | Assists | |
| Dave Chadwick | |||
Team
| Player | Yellow | Red | Subbed |
| Arthur Horsfield | |||
| John O'Rourke | |||
| Ian Davidson | |||
| Dave Chadwick | |||
| Don Masson | |||
| Jimmy Lawson | |||
| Bill Gates | |||
| Gordon Jones | |||
| Alex Smith | |||
| Neville Chapman | |||
| Des McPartland |
Subs
| Player | Yellow | Red | Subbed |