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The website of Stockport County's Historical Advisors
| Season | Lev | Rnd | Ven & Opponents | Res | Notes | |
| 1920-21 | F | f | A | Tranmere Rovers | 1-3 | |
| 1921-22 | F | s | H | TRANMERE ROVERS | 3-0 | |
| F | f | H | CREWE ALEXANDRA | 0-2 | ||
| 1922-23 | F | s | H | STALYBRIDGE CELTIC | 5-1 | |
| F | f | N | Tranmere Rovers | 1-0 | At Gresty Road, Crewe Alex | |
| 1923-24 | F | s | A | Crewe Alexandra | 0-2 | |
| 1924-25 | F | s | H | NEW BRIGHTON | 3-1 | |
| F | f | H | TRANMERE ROVERS | 2-0 | ||
| 1925-26 | F | s | A | New Brighton | 5-5 | |
| F | sr | H | NEW BRIGHTON | 2-1 | ||
| F | f | H | TRANMERE ROVERS | 1-4 | ||
| 1926-27 | F | sr | H | CREWE ALEXANDRA | 3-1 | |
| F | f | A | Chester | 0-3 | ||
| 1927-28 | F | s | H | CHESTER | 5-1 | |
| F | s | A | Crewe Alexandra | 4-4 | ||
| F | f | A | Tranmere Rovers | 2-4 | ||
| 1928-29 | F | s | A | Crewe Alexandra | 2-1 | |
| F | f | H | TRANMERE ROVERS | 3-2 | ||
| 1929-30 | F | s | H | CREWE ALEXANDRA | 2-0 | |
| F | f | A | Tranmere Rovers | 5-2 | ||
| 1930-31 | F | s | A | Macclesfield | 2-1 | Date to be confirmed |
| F | f | H | CREWE ALEXANDRA | 3-1 | ||
| 1931-32 | F | s | A | Chester | 1-4 | |
| 1933-34 | F | s | H | TRANMERE ROVERS | 4-2 | |
| F | f | A | Chester | 1-1 | ||
| F | fr | H | CHESTER | 2-0 | ||
| 1934-35 | F | s | A | Crewe Alexandra | 4-1 | |
| F | f | A | Chester | 2-4 | ||
| 1935-36 | F | s | A | Tranmere Rovers | 0-5 | |
| 1936-37 | F | s | H | TRANMERE ROVERS | 0-2 | |
| 1939-40 | F | s | A | Chester | 2-3 | |
| 1940-41 | F | s | H | CREWE ALEXANDRA | 2-1 | |
| 1941-42 | F | f | H | CHESTER | 2-4 | Carried over |
| 1942-43 | F | s,1 | A | Tranmere Rovers | 1-1 | |
| F | s,2 | H | TRANMERE ROVERS | 2-1 | ||
| F | f | A | Crewe Alexandra | 2-7 | ||
| 1943-44 | F | s,1 | H | TRANMERE ROVERS | 4-0 | |
| F | s,2 | A | Tranmere Rovers | 1-4 | Aggregate won 5-4 | |
| F | f | A | Chester | 1-6 | ||
| 1944-45 | F | s,1 | H | CREWE ALEXANDRA | 0-1 | |
| F | s,2 | A | Crewe Alexandra | 0-6 | ||
| 1945-46 | F | f,1 | A | Crewe Alexandra | 2-4 | No semi-finals as Chester and Tranmere did not enter |
| F | f,2 | H | CREWE ALEXANDRA | 0-1 | ||
| 1948-49 | F | s | H | CREWE ALEXANDRA | 5-3 | |
| F | f | H | TRANMERE ROVERS | 2-1 | After extra time | |
| 1949-50 | F | s | A | Crewe Alexandra | 0-1 | |
| 1952-53 | F | s | H | TRANMERE ROVERS | 3-1 | |
| F | f | H | CHESTER | 3-1 | ||
| 1954-55 | F | s | A | Chester | 1-2 | |
| 1955-56 | F | s | A | Chester | 1-0 | |
| F | f | H | TRANMERE ROVERS | 1-0 | ||
| 1956-57 | F | s | H | CREWE ALEXANDRA | 4-0 | |
| F | f | H | TRANMERE ROVERS | 2-0 | ||
| 1957-58 | F | s | A | Tranmere Rovers | 0-1 | |
| 1958-59 | F | s | A | Chester | 5-2 | |
| F | f,1 | H | CREWE ALEXANDRA | 1-1 | ||
| F | f,2 | A | Crewe Alexandra | 2-1 | Aggregate won 3-2 | |
| 1959-60 | F | s | A | Chester | 1-0 | |
| F | f,1 | A | Tranmere Rovers | 0-2 | ||
| F | f,2 | H | TRANMERE ROVERS | 2-0 | Aggregate drew 2-2 | |
| 1960-61 | F | fr | H | TRANMERE ROVERS | 0-1 | Carried over |
| F | s | A | Tranmere Rovers | 4-1 | ||
| F | f,1 | A | Crewe Alexandra | 0-0 | ||
| F | f,2 | H | CREWE ALEXANDRA | 1-1 | Aggregate drew 1-1, trophy shared | |
| 1961-62 | F | s | A | Chester | 1-1 | |
| F | sr | H | CHESTER | 1-0 | ||
| F | f,1 | A | Crewe Alexandra | 3-2 | ||
| F | f,2 | H | CREWE ALEXANDRA | 1-3 | Aggregate lost 4-5 | |
| 1962-63 | F | s | H | CREWE ALEXANDRA | 2-0 | |
| F | f | A | Tranmere Rovers | 1-0 | ||
| 1963-64 | F | s | H | CREWE ALEXANDRA | 1-0 | |
| F | f | A | Tranmere Rovers | 0-3 | After extra time | |
| 1964-65 | F | s | H | CHESTER | 1-2 | After extra time |
| 1965-66 | F | s | A | Crewe Alexandra | 0-1 | |
| 1966-67 | F | s | A | Tranmere Rovers | 0-1 | |
| 1967-68 | F | s | H | TRANMERE ROVERS | 2-0 | |
| F | f | A | Crewe Alexandra | 0-2 | ||
| 1968-69 | F | s | H | CHESTER | 3-1 | |
| F | f | A | Tranmere Rovers | 1-4 | ||
| 1969-70 | F | s | H | TRANMERE ROVERS | 1-0 | After extra time |
| 1970-71 | F | f | A | Crewe Alexandra | 4-1 | Carried over |
| F | s | H | TRANMERE ROVERS | 2-1 | ||
| 1971-72 | F | f | A | Chester | 1-0 | Carried over |
| F | f | A | Crewe Alexandra | 0-4 | ||
| 1972-73 | F | s | H | TRANMERE ROVERS | 2-1 | After extra time |
| 1973-74 | F | f | H | CREWE ALEXANDRA | 1-0 | Carried over |
| F | f | A | Tranmere Rovers | - | ||
| 1975-76 | F | s | H | CREWE ALEXANDRA | 2-1 | |
| 1976-77 | F | s | A | Crewe Alexandra | 1-1 | |
| F | H | CREWE ALEXANDRA | - | |||
| 1977-78 | F | g | A | Chester | 0-2 | |
| F | g | A | Crewe Alexandra | 2-0 | ||
| F | g | A | Tranmere Rovers | 2-1 | ||
| 1978-79 | F | g | A | Chester | 0-2 | |
| F | g | H | TRANMERE ROVERS | 0-1 | ||
| F | g | H | CREWE ALEXANDRA | 1-0 | ||
| 1979-80 | F | g | H | TRANMERE ROVERS | 1-2 | |
| F | g | H | CHESTER | 0-2 | ||
| 1980-81 | F | g | H | TRANMERE ROVERS | 0-2 | |
| F | g | A | Chester | 1-4 | ||
| F | g | H | CREWE ALEXANDRA | 2-3 | ||
| 2008-09 | R | 1 | A | Crewe Alexandra | 2-3 | |
| 2009-10 | R | s | H | CREWE ALEXANDRA | 2-5 | |
| 2010-11 | R | s | A | Tranmere Rovers Res | 2-0 | |
| R | f | H | CREWE ALEXANDRA RES | 1-1 | After extra time, won 4-2 on penalties | |
Details for non senior competitions may not be complete