1. Round 04/08/2018 Millwall FC - Middlesbrough FC 2:2
4. Round 07/08/2018 Middlesbrough FC - Sheffield United 3:0
2. Round 11/08/2018 Middlesbrough FC - Birmingham City 1:0
3. Round 18/08/2018 Bristol City - Middlesbrough FC 0:2
5. Round 24/08/2018 Middlesbrough FC - West Bromwich Albion 1:0
6. Round 31/08/2018 Leeds United - Middlesbrough FC 0:0
7. Round 15/09/2018 Norwich City - Middlesbrough FC 1:0
8. Round 19/09/2018 Middlesbrough FC - Bolton Wanderers 2:0
9. Round 22/09/2018 Middlesbrough FC - Swansea City 0:0
10. Round 29/09/2018 Hull City - Middlesbrough FC 1:1
11. Round 02/10/2018 Ipswich Town - Middlesbrough FC 0:2
12. Round 06/10/2018 Middlesbrough FC - Nottingham Forest 0:2
13. Round 19/10/2018 Sheffield Wednesday - Middlesbrough FC 1:2
14. Round 23/10/2018 Middlesbrough FC - Rotherham United 0:0
15. Round 27/10/2018 Middlesbrough FC - Derby County 1:1
16. Round 03/11/2018 Stoke City - Middlesbrough FC 0:0
17. Round 10/11/2018 Middlesbrough FC - Wigan Athletic 2:0
18. Round 24/11/2018 Brentford FC - Middlesbrough FC 1:2
19. Round 27/11/2018 Preston North End - Middlesbrough FC 1:1
20. Round 01/12/2018 Middlesbrough FC - Aston Villa 0:3
21. Round 08/12/2018 Middlesbrough FC - Blackburn Rovers 1:1
22. Round 15/12/2018 Queens Park Rangers - Middlesbrough FC 2:1
23. Round 22/12/2018 Reading FC - Middlesbrough FC 0:1
24. Round 26/12/2018 Middlesbrough FC - Sheffield Wednesday 0:1
25. Round 29/12/2018 Middlesbrough FC - Ipswich Town 2:0
26. Round 01/01/2019 Derby County - Middlesbrough FC 1:1
27. Round 12/01/2019 Birmingham City - Middlesbrough FC 1:2
28. Round 19/01/2019 Middlesbrough FC - Millwall FC 1:1
30. Round 02/02/2019 West Bromwich Albion - Middlesbrough FC 2:3
31. Round 09/02/2019 Middlesbrough FC - Leeds United 1:1
32. Round 13/02/2019 Sheffield United - Middlesbrough FC 1:0
33. Round 17/02/2019 Blackburn Rovers - Middlesbrough FC 0:1
34. Round 23/02/2019 Middlesbrough FC - Queens Park Rangers 2:0
35. Round 02/03/2019 Wigan Athletic - Middlesbrough FC 0:0
36. Round 09/03/2019 Middlesbrough FC - Brentford FC 1:2
37. Round 13/03/2019 Middlesbrough FC - Preston North End 1:2
38. Round 16/03/2019 Aston Villa - Middlesbrough FC 3:0
39. Round 30/03/2019 Middlesbrough FC - Norwich City 0:1
29. Round 02/04/2019 Middlesbrough FC - Bristol City 0:1
40. Round 06/04/2019 Swansea City - Middlesbrough FC 3:1
41. Round 09/04/2019 Bolton Wanderers - Middlesbrough FC 0:2
42. Round 13/04/2019 Middlesbrough FC - Hull City 1:0
43. Round 19/04/2019 Middlesbrough FC - Stoke City 1:0
44. Round 22/04/2019 Nottingham Forest - Middlesbrough FC 3:0
45. Round 27/04/2019 Middlesbrough FC - Reading FC 2:1
46. Round 05/05/2019 Rotherham United - Middlesbrough FC 1:2