1. Round 27/08/1938 Bolton Wanderers - Charlton Athletic 2:1
2. Round 31/08/1938 Manchester United - Bolton Wanderers 2:2
3. Round 03/09/1938 Portsmouth FC - Bolton Wanderers 2:1
5. Round 10/09/1938 Leeds United - Bolton Wanderers 1:2
6. Round 17/09/1938 Bolton Wanderers - Liverpool FC 3:1
7. Round 24/09/1938 Leicester City - Bolton Wanderers 0:0
8. Round 01/10/1938 Bolton Wanderers - Middlesbrough FC 4:1
9. Round 08/10/1938 Birmingham FC - Bolton Wanderers 0:2
10. Round 15/10/1938 Bolton Wanderers - Everton FC 4:2
11. Round 22/10/1938 Huddersfield Town - Bolton Wanderers 2:1
12. Round 29/10/1938 Bolton Wanderers - Arsenal FC 1:1
14. Round 12/11/1938 Bolton Wanderers - Blackpool FC 0:1
15. Round 19/11/1938 Derby County - Bolton Wanderers 3:0
17. Round 03/12/1938 Sunderland AFC - Bolton Wanderers 2:2
18. Round 10/12/1938 Bolton Wanderers - Aston Villa 1:2
19. Round 17/12/1938 Wolverhampton Wanderers - Bolton Wanderers 1:1
24. Round 14/01/1939 Bolton Wanderers - Leeds United 2:2
25. Round 25/01/1939 Liverpool FC - Bolton Wanderers 1:2
26. Round 28/01/1939 Bolton Wanderers - Leicester City 4:0
27. Round 04/02/1939 Middlesbrough FC - Bolton Wanderers 1:2
29. Round 18/02/1939 Everton FC - Bolton Wanderers 2:1
28. Round 22/02/1939 Bolton Wanderers - Birmingham FC 3:0
30. Round 25/02/1939 Bolton Wanderers - Huddersfield Town 3:2
31. Round 04/03/1939 Arsenal FC - Bolton Wanderers 3:1
32. Round 11/03/1939 Bolton Wanderers - Brentford FC 1:1
33. Round 18/03/1939 Blackpool FC - Bolton Wanderers 0:0
34. Round 25/03/1939 Bolton Wanderers - Derby County 2:1
35. Round 01/04/1939 Grimsby Town - Bolton Wanderers 1:1
37. Round 08/04/1939 Bolton Wanderers - Sunderland AFC 2:1