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CHESTER FC
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| 1919-20 | W 6-3 | Robertson-3, Flaherty, Darley, T.Walsh | L 2-5 | Law-2 |
| 1920-21 | W 4-2 | Wilding-2, Boff, Darley | L 1-5 | Daniels |
| 1921-22 | L 1-2 | Stan Taylor | L 0-1 | - |
| 1922-23 | D 1-1 | T.Cunliffe | L 0-3 | - |
| 1923-24 | D 2-2 | H.Spiby, Wignall | L 0-5 | - |
| 1924-25 | W 4-1 | King, E.Spiby, Ridgeway, Tom Jones | L 2-3 | Tom Jones, Ackerley |
| 1925-26 | D 0-0 | - | D 2-2 | Bryan, Bennett |
| 1926-27 | L 2-3 | Wignall | L 1-3 | Sharp |
| 1927-28 | W 1-0 | H.Ward | L 1-4 | A.Smith |
| 1928-29 | L 2-4 | Cooper, Roscoe | L 0-3 | - |
| 1929-30 | W 3-0 | Blood-2, Heyes | L 1-6 | Cooper |
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CHESTER RESERVES |
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| 1930-31 | L 2-4 | Ingleby, Newton | L 2-4 | Roscoe, Deans |
| 1931-32 | L 0-1 | - | L 1-8 | Dean |
| 1932-33 | W 4-1 | Scullion-3, Monoghan | L 0-5 | - |
| 1933-34 | W 4-1 | Hurst-2, F.Bell, Denton | L 1-2 | Forrester |
| 1934-35 | L 3-4 | J.Anderson, Denton, Crowder | W 3-0 | Henshall, Crowder, Nelson |
| 1935-36 | W 7-0 | Litherland-2, J.Anderson-2, Morgan, Henshall, Ashworth | L 2-10 | Ashworth, Crowder |
| 1936-37 | L 1-3 | Crewe | L 1-5 | Henshall |
| 1937-38 | W 5-0 | D.James-3, Belcher, Bright | L 1-6 | D.James |
| 1938-39 | D 1-1 | Bill Smith | L 1-4 | Roscoe |
| 1945-46 | L 1-5 | S.Lowe | L 2-3 | Saunders, James |
| 1946-47 | W 2-0 | Knowles, Sinkinson | W 3-0 | Toseland, Knowles |
| 1947-48 | L 0-2 | - | W 2-1 | A.Buckley-2 |
| 1948-49 | W 1-0 | Thorpe | L 1-4 | Thorpe |
| 1949-50 | D 2-2 | Thorpe, Wainwright | D 1-1 | Thorpe |
| 1950-51 | W 2-1 | Wrigglesworth | L 3-5 | Botothway-3 |
| 1951-52 | L 1-3 | Tilley | L 1-2 | Doyle |
| 1952-53 | L 1-4 | Reid | L 1-6 | Jones |
| 1953-54 | L 1-5 | R.Hart | L 0-6 | - |
| 1954-55 | W 2-1 | Megson-2 | D 0-0 | - |
| 1955-56 | D 2-2 | Ward-2 | W 1-0 | J.Hall |
| 1956-57 | D 1-1 | Megson | L 1-2 | Megson |
| 1957-58 | L 1-2 | J.Hilton | L 2-5 | H.Hughes, own goal |
| 1958-59 | L 0-1 | - | L 3-6 | Birnie, Dimond, Kapler |
| 1959-60 | W 2-1 | Gordon, T.Burke | L 1-2 | B.Taylor |
| 1960-61 | W 5-2 | Gordon-3, Gaskell, B.Hughes | L 0-2 | - |
| 1961-62 | W 5-2 | McCreadie-2, B.Hughes, Willis, Ashton | L 0-2 | - |
| 1962-63 | W 2-0 | T.Burke-2 | W 1-0 | T.Burke |
| 1963-64 | L 2-3 | T.Burke, Rowley | L 2-3 | Evison-2 |
| 1964-65 | D 0-0 | - | L 1-5 | Grimsditch |
| 1965-66 | W 3-0 | K.Fletcher, Maughan, own goal | D 1-1 | Maughan |
| 1966-67 | W 3-1 | McKay-2, own goal | W 3-0 | Dowthwaite, own goals-2 |
| 1967-68 | W 3-1 | K.Burke, Boss, Lyon | W 4-1 | T.Burke, M.Brennan |
| 1968-69 | W 8-0 | Mason-3, B.Birtwistle--2, Lyon, Dowthwaite, Dickenson | W 2-1 | Hainsworth, Maughan |
