| L2 | 2020-2021 | 20/02/2021 | Southend United | 0-1 | Bolton Wanderers | Shaun Miller | Highlights | Unknown | Win |
| L2 | 2020-2021 | 01/12/2020 | Bolton Wanderers | 3-0 | Southend United | Nathan Delfouneso, Eoin Doyle, Eoin Doyle | Highlights | Unknown | Win |
| L1 | 2019-2020 | 21/12/2019 | Bolton Wanderers | 3-2 | Southend United | Joe Dodoo, Luke Murphy, Daryl Murphy | Highlights | 6,965 | Win |
| L1 | 2016-2017 | 04/04/2017 | Southend United | 0-1 | Bolton Wanderers | Mark Beevers | Highlights | 9,340 | Win |
| L1 | 2016-2017 | 03/09/2016 | Bolton Wanderers | 1-1 | Southend United | Keshi Anderson | Highlights | 13,519 | Draw |
| D1 | 1996-1997 | 28/12/1996 | Bolton Wanderers | 3-1 | Southend United | Sellars 2, McGinlay (pen) | | 16,357 | Win |
| D1 | 1996-1997 | 07/09/1996 | Southend United | 5-2 | Bolton Wanderers | Blake, McGinlay | | 4,475 | Loss |
| D1 | 1994-1995 | 04/03/1995 | Bolton Wanderers | 3-0 | Southend United | Thompson A, Lee D, McAteer J | | 10,766 | Win |
| D1 | 1994-1995 | 24/09/1994 | Southend United | 2-1 | Bolton Wanderers | Sneekes | | 4,507 | Loss |
| D1 | 1993-1994 | 12/04/1994 | Bolton Wanderers | 0-2 | Southend United | | | 7,140 | Loss |
| D1 | 1993-1994 | 12/01/1994 | Southend United | 0-2 | Bolton Wanderers | Stubbs, McGinlay | | 4,969 | Win |
| D3 | 1990-1991 | 30/03/1991 | Bolton Wanderers | 1-0 | Southend United | Darby | | 10,666 | Win |
| D3 | 1990-1991 | 26/12/1990 | Southend United | 1-1 | Bolton Wanderers | Green | | 7,539 | Draw |
| D3 | 1988-1989 | 18/03/1989 | Bolton Wanderers | 0-0 | Southend United | | | 3,505 | Draw |
| D3 | 1988-1989 | 27/08/1988 | Southend United | 2-0 | Bolton Wanderers | | | 4,075 | Loss |
| D3 | 1983-1984 | 06/02/1984 | Southend United | 0-1 | Bolton Wanderers | Caldwell | | 1,594 | Win |
| D3 | 1983-1984 | 29/10/1983 | Bolton Wanderers | 2-0 | Southend United | Caldwell 2 | | 5,366 | Win |
| LC2L2 | 1979-1980 | 03/09/1979 | Southend United | 0-0 | Bolton Wanderers | | | 9,140 | Draw |
| LC2L1 | 1979-1980 | 28/08/1979 | Bolton Wanderers | 1-2 | Southend United | Gowling | | 7,861 | Loss |
| D3 | 1972-1973 | 24/03/1973 | Southend United | 1-1 | Bolton Wanderers | Jones P | | 8,046 | Draw |
| D3 | 1972-1973 | 28/10/1972 | Bolton Wanderers | 1-1 | Southend United | Phillips R | | 7,342 | Draw |