Portsmouth 0 Middlesbrough 1
Outcome: Won
Date: 3/8/1969
Manager: Stan Anderson
Attendance: 23982
Competition: DivisionTwo
Played at: Ayresome Park
Goals:
| Goals | Time | Assists | |
| Johnny Crossan | |||
Team
| Player | Yellow | Red | Subbed |
| John Hickton | |||
| Stan Webb | |||
| Johnny Crossan | |||
| Eric McMordie | |||
| George Smith | |||
| Dave Chadwick | |||
| Frank Spraggon | |||
| Alan Moody | |||
| Gordon Jones | |||
| Dickie Rooks | |||
| Willie Whigham |
Subs
| Player | Yellow | Red | Subbed |