| L1 | 2022-2023 | 17/03/2023 | Sheffield Wednesday | 1-1 | Bolton Wanderers | Victor Adeboyejo | Highlights | 29,230 | Draw |
| L1 | 2022-2023 | 20/08/2022 | Bolton Wanderers | 0-2 | Sheffield Wednesday | | Highlights | 22,023 | Loss |
| L1 | 2021-2022 | 09/04/2022 | Bolton Wanderers | 1-1 | Sheffield Wednesday | MJ Williams | Highlights | 19,164 | Draw |
| L1 | 2021-2022 | 09/10/2021 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | Highlights | 23,692 | Loss |
| C | 2018-2019 | 12/03/2019 | Bolton Wanderers | 0-2 | Sheffield Wednesday | | Highlights | 13,624 | Loss |
| C | 2018-2019 | 27/11/2018 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | Highlights | 20,861 | Loss |
| C | 2017-2018 | 10/03/2018 | Sheffield Wednesday | 1-1 | Bolton Wanderers | Aaron Wilbraham | Highlights | 26,809 | Draw |
| C | 2017-2018 | 14/10/2017 | Bolton Wanderers | 2-1 | Sheffield Wednesday | Sammi Ameobi, Own Goal | Highlights | 17,967 | Win |
| LC2 | 2017-2018 | 22/08/2017 | Bolton Wanderers | 3-2 | Sheffield Wednesday | Dorian Dervite, Adam Armstrong, Jem Karacan | Highlights | 6,385 | Win |
| C | 2015-2016 | 12/01/2016 | Sheffield Wednesday | 3-2 | Bolton Wanderers | Gary Madine, David Wheater | Highlights | 20,757 | Loss |
| C | 2015-2016 | 15/09/2015 | Bolton Wanderers | 0-0 | Sheffield Wednesday | | Highlights | 14,438 | Draw |
| C | 2014-2015 | 17/01/2015 | Sheffield Wednesday | 1-2 | Bolton Wanderers | Feeney, Pratley | Highlights | 22,617 | Win |
| C | 2014-2015 | 13/09/2014 | Bolton Wanderers | 0-0 | Sheffield Wednesday | | Highlights | 15,799 | Draw |
| C | 2013-2014 | 26/04/2014 | Sheffield Wednesday | 1-3 | Bolton Wanderers | Danns, Chung-Yong, Trotter | Highlights | 23,070 | Win |
| C | 2013-2014 | 19/10/2013 | Bolton Wanderers | 1-1 | Sheffield Wednesday | Beckford | Highlights | 17,177 | Draw |
| C | 2012-2013 | 26/12/2012 | Bolton Wanderers | 0-1 | Sheffield Wednesday | | | 22,292 | Loss |
| C | 2012-2013 | 22/09/2012 | Sheffield Wednesday | 1-2 | Bolton Wanderers | Alonso, Davies M | | 26,598 | Win |
| D1 | 2000-2001 | 20/01/2001 | Sheffield Wednesday | 0-3 | Bolton Wanderers | Gardner, Ricketts, Marshall | | 17,638 | Win |
| D1 | 2000-2001 | 26/12/2000 | Bolton Wanderers | 2-0 | Sheffield Wednesday | Holdsworth, Hendry | | 21,316 | Win |
| LC4 | 1999-2000 | 30/11/1999 | Bolton Wanderers | 1-0 | Sheffield Wednesday | Elliott R | | 12,543 | Win |
| PL | 1997-1998 | 14/03/1998 | Bolton Wanderers | 3-2 | Sheffield Wednesday | Frandsen, Blake, Thompson A (pen) | | 24,847 | Win |
| PL | 1997-1998 | 08/11/1997 | Sheffield Wednesday | 5-0 | Bolton Wanderers | | | 25,027 | Loss |
| PL | 1995-1996 | 23/03/1996 | Bolton Wanderers | 2-1 | Sheffield Wednesday | Sellars, Curcic | | 18,368 | Win |
| PL | 1995-1996 | 01/01/1996 | Sheffield Wednesday | 4-2 | Bolton Wanderers | Curcic, Taggart | | 24,872 | Loss |
| LC2L2 | 1993-1994 | 06/10/1993 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | 16,194 | Loss |
| LC2L1 | 1993-1994 | 21/09/1993 | Bolton Wanderers | 1-1 | Sheffield Wednesday | Kelly (pen) | | 11,590 | Draw |
| D2 | 1982-1983 | 09/04/1983 | Bolton Wanderers | 0-2 | Sheffield Wednesday | | | 6,408 | Loss |
| D2 | 1982-1983 | 07/09/1982 | Sheffield Wednesday | 3-1 | Bolton Wanderers | Henry | | 17,307 | Loss |
| D2 | 1981-1982 | 08/05/1982 | Bolton Wanderers | 3-1 | Sheffield Wednesday | Chandler, Gowling, Henry | | 13,656 | Win |
| D2 | 1981-1982 | 16/02/1982 | Sheffield Wednesday | 0-1 | Bolton Wanderers | Foster W | | 16,555 | Win |
| D2 | 1980-1981 | 11/11/1980 | Sheffield Wednesday | 2-0 | Bolton Wanderers | | | 16,262 | Loss |
| D2 | 1980-1981 | 19/08/1980 | Bolton Wanderers | 0-0 | Sheffield Wednesday | | | 15,926 | Draw |
| D2 | 1974-1975 | 26/12/1974 | Sheffield Wednesday | 0-2 | Bolton Wanderers | Lee S, Curran | | 17,153 | Win |
| D2 | 1974-1975 | 14/09/1974 | Bolton Wanderers | 0-1 | Sheffield Wednesday | | | 14,597 | Loss |
| D2 | 1973-1974 | 27/04/1974 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | 23,264 | Loss |
| D2 | 1973-1974 | 16/02/1974 | Bolton Wanderers | 4-2 | Sheffield Wednesday | Ritson, Byrom 2, Jones G | | 13,405 | Win |
| LC2 | 1972-1973 | 06/09/1972 | Sheffield Wednesday | 2-0 | Bolton Wanderers | | | 15,903 | Loss |
| D2 | 1970-1971 | 02/09/1970 | Sheffield Wednesday | 1-1 | Bolton Wanderers | Hunt R | | 12,420 | Draw |
| D2 | 1970-1971 | 19/08/1970 | Bolton Wanderers | 2-1 | Sheffield Wednesday | Ritson, Hunt R | | 13,462 | Win |
| D1 | 1963-1964 | 28/12/1963 | Bolton Wanderers | 3-0 | Sheffield Wednesday | Lee F, Davies W, Deakin P | | 12,376 | Win |
| D1 | 1963-1964 | 26/12/1963 | Sheffield Wednesday | 3-0 | Bolton Wanderers | | | 30,532 | Loss |
| D1 | 1962-1963 | 06/05/1963 | Bolton Wanderers | 0-4 | Sheffield Wednesday | | | 12,905 | Loss |
| D1 | 1962-1963 | 18/08/1962 | Sheffield Wednesday | 1-1 | Bolton Wanderers | Davies W | | 28,036 | Draw |
| D1 | 1961-1962 | 30/08/1961 | Bolton Wanderers | 4-3 | Sheffield Wednesday | Holden D, McAdams, Hill 2 | | 19,559 | Win |
| D1 | 1961-1962 | 23/08/1961 | Sheffield Wednesday | 4-2 | Bolton Wanderers | Holden D, McAdams | | 35,460 | Loss |
| D1 | 1960-1961 | 18/03/1961 | Bolton Wanderers | 0-1 | Sheffield Wednesday | | | 19,418 | Loss |
| D1 | 1960-1961 | 29/10/1960 | Sheffield Wednesday | 2-0 | Bolton Wanderers | | | 25,708 | Loss |
| D1 | 1959-1960 | 24/02/1960 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | 34,464 | Loss |
| D1 | 1959-1960 | 03/10/1959 | Bolton Wanderers | 1-0 | Sheffield Wednesday | Parry R | | 23,990 | Win |
| D1 | 1957-1958 | 15/03/1958 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | 24,085 | Loss |
| D1 | 1957-1958 | 02/11/1957 | Bolton Wanderers | 5-4 | Sheffield Wednesday | Holden D, Lofthouse 2, Parry R, Birch | | 18,072 | Win |
| D1 | 1956-1957 | 16/03/1957 | Bolton Wanderers | 3-2 | Sheffield Wednesday | Lofthouse, Ball, Hennin* (some records credit Lofthouse) | | 18,424 | Win |
| D1 | 1956-1957 | 03/11/1956 | Sheffield Wednesday | 1-2 | Bolton Wanderers | Gubbins, Allcock | | 23,968 | Win |
| D1 | 1954-1955 | 11/04/1955 | Sheffield Wednesday | 3-2 | Bolton Wanderers | Lofthouse 2 | | 16,569 | Loss |
| D1 | 1954-1955 | 08/04/1955 | Bolton Wanderers | 2-2 | Sheffield Wednesday | Moir, Barrass | | 22,909 | Draw |
| FACQFR | 1953-1954 | 17/03/1954 | Bolton Wanderers | 0-2 | Sheffield Wednesday | | | 52,568 | Loss |
| FACQF | 1953-1954 | 13/03/1954 | Sheffield Wednesday | 1-1 | Bolton Wanderers | Moir (pen) | | 65,000 | Draw |
| D1 | 1953-1954 | 16/09/1953 | Sheffield Wednesday | 2-1 | Bolton Wanderers | Hassall | | 26,025 | Loss |
| D1 | 1953-1954 | 09/09/1953 | Bolton Wanderers | 2-1 | Sheffield Wednesday | Moir, Hassall (pen) | | 31,143 | Win |
| D1 | 1952-1953 | 11/04/1953 | Sheffield Wednesday | 1-1 | Bolton Wanderers | Lofthouse | | 39,893 | Draw |
| D1 | 1952-1953 | 22/11/1952 | Bolton Wanderers | 1-1 | Sheffield Wednesday | Moir | | 34,435 | Draw |
| D1 | 1950-1951 | 14/04/1951 | Bolton Wanderers | 0-1 | Sheffield Wednesday | | | 19,956 | Loss |
| D1 | 1950-1951 | 25/11/1950 | Sheffield Wednesday | 3-4 | Bolton Wanderers | Lofthouse 2, Webster 2 | | 37,053 | Win |
| D1 | 1936-1937 | 29/03/1937 | Sheffield Wednesday | 2-0 | Bolton Wanderers | | | 30,859 | Loss |
| D1 | 1936-1937 | 26/03/1937 | Bolton Wanderers | 1-0 | Sheffield Wednesday | Milsom | | 26,780 | Win |
| D1 | 1935-1936 | 09/09/1935 | Sheffield Wednesday | 2-2 | Bolton Wanderers | Goslin, Westwood | | 12,912 | Draw |
| D1 | 1935-1936 | 02/09/1935 | Bolton Wanderers | 1-1 | Sheffield Wednesday | Eastham | | 21,655 | Draw |
| D1 | 1932-1933 | 29/04/1933 | Sheffield Wednesday | 2-0 | Bolton Wanderers | | | 4,810 | Loss |
| D1 | 1932-1933 | 17/12/1932 | Bolton Wanderers | 3-0 | Sheffield Wednesday | Milsom 3 | | 11,409 | Win |
| D1 | 1931-1932 | 16/01/1932 | Bolton Wanderers | 2-4 | Sheffield Wednesday | Gibson, Blackmore | | 9,694 | Loss |
| D1 | 1931-1932 | 05/09/1931 | Sheffield Wednesday | 7-1 | Bolton Wanderers | Blackmore | | 14,544 | Loss |
| D1 | 1930-1931 | 07/02/1931 | Bolton Wanderers | 2-2 | Sheffield Wednesday | Blackmore, Tait | | 19,594 | Draw |
| D1 | 1930-1931 | 04/10/1930 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | 21,310 | Loss |
| D1 | 1929-1930 | 25/09/1929 | Bolton Wanderers | 1-3 | Sheffield Wednesday | Gibson | | 11,136 | Loss |
| D1 | 1929-1930 | 02/09/1929 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | 26,480 | Loss |
| D1 | 1928-1929 | 09/02/1929 | Bolton Wanderers | 2-2 | Sheffield Wednesday | Blackmore 2 | | 22,387 | Draw |
| D1 | 1928-1929 | 29/09/1928 | Sheffield Wednesday | 0-0 | Bolton Wanderers | | | 25,098 | Draw |
| D1 | 1927-1928 | 29/02/1928 | Bolton Wanderers | 2-0 | Sheffield Wednesday | Jack D 2 | | 9,786 | Win |
| D1 | 1927-1928 | 17/09/1927 | Sheffield Wednesday | 3-0 | Bolton Wanderers | | | 19,111 | Loss |
| D1 | 1926-1927 | 02/04/1927 | Bolton Wanderers | 3-2 | Sheffield Wednesday | Blackmore, Marsden (og), Butler W | | 16,195 | Win |
| D1 | 1926-1927 | 13/11/1926 | Sheffield Wednesday | 2-1 | Bolton Wanderers | Smith J | | 21,033 | Loss |
| D1 | 1919-1920 | 05/04/1920 | Sheffield Wednesday | 0-2 | Bolton Wanderers | Roberts F, Smith J | | Unknown | Win |
| D1 | 1919-1920 | 01/01/1920 | Bolton Wanderers | 2-0 | Sheffield Wednesday | Roberts F 2 | | Unknown | Win |
| D1 | 1914-1915 | 01/03/1915 | Sheffield Wednesday | 7-0 | Bolton Wanderers | | | Unknown | Loss |
| D1 | 1914-1915 | 17/10/1914 | Bolton Wanderers | 0-3 | Sheffield Wednesday | | | Unknown | Loss |
| D1 | 1913-1914 | 29/12/1913 | Sheffield Wednesday | 1-1 | Bolton Wanderers | Lillycrop | | Unknown | Draw |
| D1 | 1913-1914 | 01/09/1913 | Bolton Wanderers | 0-1 | Sheffield Wednesday | | | Unknown | Loss |
| D1 | 1912-1913 | 24/02/1913 | Sheffield Wednesday | 2-2 | Bolton Wanderers | Smith J, Feebury | | Unknown | Draw |
| D1 | 1912-1913 | 19/10/1912 | Bolton Wanderers | 3-0 | Sheffield Wednesday | Smith J, Barber, Worrall (og) | | Unknown | Win |
| D1 | 1911-1912 | 23/03/1912 | Sheffield Wednesday | 0-1 | Bolton Wanderers | Smith J | | Unknown | Win |
| D1 | 1911-1912 | 18/11/1911 | Bolton Wanderers | 4-2 | Sheffield Wednesday | Smith J 2, Hilton, Stokes | | Unknown | Win |
| D1 | 1909-1910 | 02/04/1910 | Sheffield Wednesday | 0-0 | Bolton Wanderers | | | Unknown | Draw |
| D1 | 1909-1910 | 03/01/1910 | Bolton Wanderers | 0-2 | Sheffield Wednesday | | | Unknown | Loss |
| D1 | 1907-1908 | 11/04/1908 | Bolton Wanderers | 2-1 | Sheffield Wednesday | Shepherd, Stokes | | Unknown | Win |
| D1 | 1907-1908 | 14/12/1907 | Sheffield Wednesday | 5-2 | Bolton Wanderers | White, Shepherd | | Unknown | Loss |
| D1 | 1906-1907 | 16/03/1907 | Sheffield Wednesday | 2-0 | Bolton Wanderers | | | Unknown | Loss |
| D1 | 1906-1907 | 10/11/1906 | Bolton Wanderers | 0-0 | Sheffield Wednesday | | | Unknown | Draw |
| D1 | 1905-1906 | 17/03/1906 | Bolton Wanderers | 1-0 | Sheffield Wednesday | Marsh S | | Unknown | Win |
| D1 | 1905-1906 | 11/11/1905 | Sheffield Wednesday | 1-2 | Bolton Wanderers | McEwan, Stokes | | Unknown | Win |
| D1 | 1902-1903 | 03/01/1903 | Sheffield Wednesday | 3-0 | Bolton Wanderers | | | Unknown | Loss |
| D1 | 1902-1903 | 06/09/1902 | Bolton Wanderers | 0-2 | Sheffield Wednesday | | | Unknown | Loss |
| D1 | 1901-1902 | 18/01/1902 | Bolton Wanderers | 3-1 | Sheffield Wednesday | Bannister W, Bell L, Freebairn | | Unknown | Win |
| D1 | 1901-1902 | 21/09/1901 | Sheffield Wednesday | 5-1 | Bolton Wanderers | Bell L | | Unknown | Loss |
| D1 | 1900-1901 | 05/01/1901 | Bolton Wanderers | 1-1 | Sheffield Wednesday | Freebairn | | Unknown | Draw |
| D1 | 1900-1901 | 08/09/1900 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | Unknown | Loss |
| FAC1 | 1899-1900 | 27/01/1900 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | 12,390 | Loss |
| D2 | 1899-1900 | 13/01/1900 | Bolton Wanderers | 1-0 | Sheffield Wednesday | Jack R | | 12,325 | Win |
| D2 | 1899-1900 | 16/09/1899 | Sheffield Wednesday | 2-1 | Bolton Wanderers | Opponent (og) | | Unknown | Loss |
| D1 | 1898-1899 | 14/01/1899 | Sheffield Wednesday | 1-0 | Bolton Wanderers | | | Unknown | Loss |
| D1 | 1898-1899 | 17/09/1898 | Bolton Wanderers | 0-0 | Sheffield Wednesday | | | Unknown | Draw |
| D1 | 1897-1898 | 27/11/1897 | Sheffield Wednesday | 3-0 | Bolton Wanderers | | | Unknown | Loss |
| D1 | 1897-1898 | 09/10/1897 | Bolton Wanderers | 0-3 | Sheffield Wednesday | | | Unknown | Loss |
| D1 | 1896-1897 | 10/04/1897 | Bolton Wanderers | 2-1 | Sheffield Wednesday | Cassidy J, Miller T | | Unknown | Win |
| D1 | 1896-1897 | 27/02/1897 | Sheffield Wednesday | 0-0 | Bolton Wanderers | | | Unknown | Draw |
| D1 | 1895-1896 | 25/04/1896 | Bolton Wanderers | 2-0 | Sheffield Wednesday | Jack R, Cassidy J | | Unknown | Win |
| FACSFR | 1895-1896 | 28/03/1896 | Bolton Wanderers | 1-3 | Sheffield Wednesday | Tannahill (played at Town Ground, Nottingham) | | Unknown | Loss |
| FACSF | 1895-1896 | 21/03/1896 | Bolton Wanderers | 1-1 | Sheffield Wednesday | Tannahill (played at Goodison Park, Liverpool) | | Unknown | Draw |
| D1 | 1895-1896 | 02/11/1895 | Sheffield Wednesday | 1-1 | Bolton Wanderers | Joyce W | | Unknown | Draw |
| D1 | 1894-1895 | 07/01/1895 | Bolton Wanderers | 2-2 | Sheffield Wednesday | Paton 2 | | Unknown | Draw |
| D1 | 1894-1895 | 22/09/1894 | Sheffield Wednesday | 2-1 | Bolton Wanderers | Andrews | | Unknown | Loss |
| FACSF | 1893-1894 | 10/03/1894 | Bolton Wanderers | 2-1 | Sheffield Wednesday | Bentley H 2 (played at Fallowfield, Manchester) | | Unknown | Win |
| D1 | 1893-1894 | 25/12/1893 | Bolton Wanderers | 1-1 | Sheffield Wednesday | Cassidy J | | Unknown | Draw |
| D1 | 1893-1894 | 16/12/1893 | Sheffield Wednesday | 2-1 | Bolton Wanderers | Cassidy J | | Unknown | Loss |
| D1 | 1892-1893 | 05/11/1892 | Sheffield Wednesday | 4-2 | Bolton Wanderers | Wilson J, Dickenson | | Unknown | Loss |
| D1 | 1892-1893 | 17/09/1892 | Bolton Wanderers | 1-0 | Sheffield Wednesday | Dickenson | | Unknown | Win |
| FAC1R | 1891-1892 | 23/01/1892 | Sheffield Wednesday | 4-1 | Bolton Wanderers | Jones D | | Unknown | Loss |
| FAC1 | 1891-1892 | 16/01/1892 | Sheffield Wednesday | 2-1 | Bolton Wanderers | Munro (replay ordered, ground unfit) | | Unknown | Loss |
| FACSF | 1889-1890 | 08/03/1890 | Bolton Wanderers | 1-2 | Sheffield Wednesday | McNee (played at Perry Barr, Birmingham) | | Unknown | Loss |