| L1 | 2022-2023 | 11/03/2023 | Bolton Wanderers | 0-2 | Ipswich Town | | Highlights | 20,532 | Loss |
| L1 | 2022-2023 | 30/07/2022 | Ipswich Town | 1-1 | Bolton Wanderers | Aaron Morley | Highlights | 26,688 | Draw |
| L1 | 2021-2022 | 15/01/2022 | Bolton Wanderers | 2-0 | Ipswich Town | Keiran Lee, Aladapo Afolayan | Highlights | 14,020 | Win |
| L1 | 2021-2022 | 11/09/2021 | Ipswich Town | 2-5 | Bolton Wanderers | Dapo Afolyan, Eoin Doyle, Dapo Afolayan, Josh Sheehan, George Johnstone | Highlights | 19,267 | Win |
| L1 | 2019-2020 | 24/08/2019 | Bolton Wanderers | 0-5 | Ipswich Town | | Highlights | 5,454 | Loss |
| C | 2018-2019 | 06/04/2019 | Bolton Wanderers | 1-2 | Ipswich Town | Own Goal | Highlights | 17,811 | Loss |
| C | 2018-2019 | 22/09/2018 | Ipswich Town | 0-0 | Bolton Wanderers | | Highlights | 14,755 | Draw |
| C | 2017-2018 | 20/01/2018 | Bolton Wanderers | 1-1 | Ipswich Town | Gary Madine | Highlights | 13,870 | Draw |
| C | 2017-2018 | 16/09/2017 | Ipswich Town | 2-0 | Bolton Wanderers | | Highlights | 14,164 | Loss |
| C | 2015-2016 | 08/03/2016 | Bolton Wanderers | 2-2 | Ipswich Town | Lawrie Wilson, Stephen Dobbie | Highlights | 12,681 | Draw |
| C | 2015-2016 | 03/11/2015 | Ipswich Town | 2-0 | Bolton Wanderers | | Highlights | 17,017 | Loss |
| C | 2014-2015 | 17/03/2015 | Ipswich Town | 1-0 | Bolton Wanderers | | Highlights | 16,923 | Loss |
| C | 2014-2015 | 13/12/2014 | Bolton Wanderers | 0-0 | Ipswich Town | | Highlights | 15,186 | Draw |
| C | 2013-2014 | 01/02/2014 | Ipswich Town | 1-0 | Bolton Wanderers | | Highlights | 15,429 | Loss |
| C | 2013-2014 | 26/10/2013 | Bolton Wanderers | 1-1 | Ipswich Town | Medo | Highlights | 15,222 | Draw |
| C | 2012-2013 | 16/03/2013 | Ipswich Town | 1-0 | Bolton Wanderers | | | 17,034 | Loss |
| C | 2012-2013 | 01/12/2012 | Bolton Wanderers | 1-2 | Ipswich Town | Davies M | | 17,208 | Loss |
| FAC3 | 2004-2005 | 08/01/2005 | Ipswich Town | 1-3 | Bolton Wanderers | Giannakopoulos, Pedersen 2 | | 20,080 | Win |
| PL | 2001-2002 | 06/04/2002 | Bolton Wanderers | 4-1 | Ipswich Town | Bobic 3, Djorkaeff | Highlights | 25,817 | Win |
| PL | 2001-2002 | 18/11/2001 | Ipswich Town | 1-2 | Bolton Wanderers | Bergsson, Ricketts | | 22,335 | Win |
| D1PSFL2 | 1999-2000 | 17/05/2000 | Ipswich Town | 5-3 | Bolton Wanderers | Holdsworth 2, Johnston A (aet) | | 21,543 | Loss |
| D1PSFL1 | 1999-2000 | 14/05/2000 | Bolton Wanderers | 2-2 | Ipswich Town | Holdsworth, Gudjohnsen | | 18,814 | Draw |
| D1 | 1999-2000 | 22/01/2000 | Bolton Wanderers | 1-1 | Ipswich Town | Holdsworth | | 13,266 | Draw |
| D1 | 1999-2000 | 21/08/1999 | Ipswich Town | 1-0 | Bolton Wanderers | | | 17,696 | Loss |
| D1PSFL2 | 1998-1999 | 19/05/1999 | Ipswich Town | 4-3 | Bolton Wanderers | Taylor B 2, Frandsen (aet) | | 21,755 | Loss |
| D1PSFL1 | 1998-1999 | 16/05/1999 | Bolton Wanderers | 1-0 | Ipswich Town | Johansen | | 18,295 | Win |
| D1 | 1998-1999 | 17/04/1999 | Bolton Wanderers | 2-0 | Ipswich Town | Taylor B, Gudjohnsen | | 19,894 | Win |
| D1 | 1998-1999 | 21/11/1998 | Ipswich Town | 0-1 | Bolton Wanderers | Taylor B | | 17,225 | Win |
| D1 | 1996-1997 | 15/03/1997 | Ipswich Town | 0-1 | Bolton Wanderers | McGinlay | | 16,187 | Win |
| D1 | 1996-1997 | 14/12/1996 | Bolton Wanderers | 1-2 | Ipswich Town | Bergsson | | 13,314 | Loss |
| LC2L2 | 1994-1995 | 05/10/1994 | Bolton Wanderers | 1-0 | Ipswich Town | Sneekes | | 8,212 | Win |
| LC2L1 | 1994-1995 | 21/09/1994 | Ipswich Town | 0-3 | Bolton Wanderers | McAteer J, McGinlay, Thompson A | | 7,787 | Win |
| D1 | 1979-1980 | 26/04/1980 | Ipswich Town | 1-0 | Bolton Wanderers | | | 21,447 | Loss |
| D1 | 1979-1980 | 15/12/1979 | Bolton Wanderers | 0-1 | Ipswich Town | | | 10,929 | Loss |
| D1 | 1978-1979 | 21/04/1979 | Bolton Wanderers | 2-3 | Ipswich Town | Worthington F, Allardyce | | 20,073 | Loss |
| D1 | 1978-1979 | 16/12/1978 | Ipswich Town | 3-0 | Bolton Wanderers | | | 16,953 | Loss |
| D2 | 1967-1968 | 09/03/1968 | Bolton Wanderers | 1-2 | Ipswich Town | Greaves | | 8,695 | Loss |
| D2 | 1967-1968 | 09/09/1967 | Ipswich Town | 1-1 | Bolton Wanderers | Lee F | | 14,903 | Draw |
| D2 | 1966-1967 | 11/02/1967 | Bolton Wanderers | 1-1 | Ipswich Town | Taylor G | | 12,565 | Draw |
| D2 | 1966-1967 | 01/10/1966 | Ipswich Town | 2-2 | Bolton Wanderers | Lee F, Davies W | | 16,019 | Draw |
| D2 | 1965-1966 | 12/03/1966 | Bolton Wanderers | 3-1 | Ipswich Town | Lee F, Hill, Davies W | | 9,180 | Win |
| D2 | 1965-1966 | 18/09/1965 | Ipswich Town | 2-0 | Bolton Wanderers | | | 12,775 | Loss |
| D2 | 1964-1965 | 23/01/1965 | Bolton Wanderers | 0-0 | Ipswich Town | | | 13,557 | Draw |
| D2 | 1964-1965 | 19/09/1964 | Ipswich Town | 1-4 | Bolton Wanderers | Lee F 2, Thrower (og), Elsworthy (og) | | 12,558 | Win |
| D1 | 1963-1964 | 01/10/1963 | Ipswich Town | 1-3 | Bolton Wanderers | Butler D, Taylor G 2 | | 11,363 | Win |
| D1 | 1963-1964 | 18/09/1963 | Bolton Wanderers | 6-0 | Ipswich Town | Pilkington, Davies W 2, Lennard 2, Taylor G | | 12,917 | Win |
| D1 | 1962-1963 | 17/05/1963 | Ipswich Town | 4-1 | Bolton Wanderers | Davies W | | 19,088 | Loss |
| D1 | 1962-1963 | 08/09/1962 | Bolton Wanderers | 1-3 | Ipswich Town | Holden D | | 17,790 | Loss |
| D1 | 1961-1962 | 16/12/1961 | Ipswich Town | 2-1 | Bolton Wanderers | Holden D | | 16,587 | Loss |
| D1 | 1961-1962 | 19/08/1961 | Bolton Wanderers | 0-0 | Ipswich Town | | | 16,708 | Draw |