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
13. Round 05/11/1938 Brentford FC - Bolton Wanderers 2:2
14. Round 12/11/1938 Bolton Wanderers - Blackpool FC 0:1
15. Round 19/11/1938 Derby County - Bolton Wanderers 3:0
16. Round 26/11/1938 Bolton Wanderers - Grimsby Town 1:1
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
20. Round 24/12/1938 Charlton Athletic - Bolton Wanderers 2:1
22. Round 27/12/1938 Preston North End - Bolton Wanderers 2:2
23. Round 31/12/1938 Bolton Wanderers - Portsmouth FC 5:1
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
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
38. Round 10/04/1939 Stoke City - Bolton Wanderers 4:1
41. Round 29/04/1939 Bolton Wanderers - Manchester United 0:0
42. Round 06/05/1939 Chelsea FC - Bolton Wanderers 1:1