 |
 |
| Pr. League | 02.01.1939 | Middlesbrough FC | - | Liverpool FC | 3:0 | 25.309 |
| Pr. League | 25.01.1939 | Middlesbrough FC | - | Preston North End | 2:2 | 9.262 |
| Pr. League | 04.02.1939 | Middlesbrough FC | - | Bolton Wanderers | 1:2 | 16.416 |
| Pr. League | 25.02.1939 | Middlesbrough FC | - | Sunderland AFC | 3:0 | 23.882 |
| Pr. League | 11.03.1939 | Middlesbrough FC | - | Everton FC | 4:4 | 20.014 |
| Pr. League | 29.03.1939 | Middlesbrough FC | - | Portsmouth FC | 8:2 | 6.116 |
| Pr. League | 08.04.1939 | Middlesbrough FC | - | Brentford FC | 3:1 | 18.191 |
| Pr. League | 10.04.1939 | Middlesbrough FC | - | Leicester City | 3:2 | 19.764 |
| Pr. League | 22.04.1939 | Middlesbrough FC | - | Derby County | 2:0 | 13.673 |
England