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The website of Stockport County's Historical Advisors
| Season | Lev | Rnd | Ven & Opponents | Res | Notes | |
| 1898-99 | F | 1 | A | Nantwich | 1-3 | |
| 1904-05 | F | 2 | H | CREWE ALEXANDRA | 2-0 | Excused round 1 |
| F | 3 | A | Altrincham | 0-0 | Home game switched | |
| F | 3r | A | Altrincham | 0-1 | ||
| 1905-06 | F | 3 | A | Helsby Athletic | 3-1 | Excused rounds 1 and 2 |
| F | 4 | A | Altrincham | 1-1 | ||
| F | 4r | H | ALTRINCHAM | 4-3 | ||
| F | s | H | CREWE ALEXANDRA | 2-0 | At Pollitts Field, Altrincham | |
| F | f | N | Northwich Victoria | 2-1 | At Gresty Road, Crewe Alex | |
| 1906-07 | F | 3 | A | Sale Holmfield | 0-3 | Exempt from previous rounds |
| 1908-09 | F | 3 | A | Hyde | 2-2 | Home game switched. Excused round 1, bye in round 2 |
| F | 3r | A | Hyde | 4-1 | ||
| F | 4 | A | Altrincham | 3-4 | ||
| 1909-10 | F | 2 | H | HYDE | 2-1 | Excused round 1 |
| F | 3 | A | Hazel Grove | 4-1 | ||
| F | 4 | A | Chester | 0-0 | ||
| F | 4r | H | CHESTER | 3-1 | ||
| F | s | A | Macclesfield | 1-2 | ||
| 1910-11 | F | 3 | A | Hazel Grove | 1-1 | Bye in previosu rounds |
| F | 1r | H | HAZEL GROVE | 7-0 | ||
| F | 2 | A | Macclesfield | 0-0 | ||
| F | 2r | A | Macclesfield | 0-2 | Home game switched due to ground closure | |
| 1911-12 | F | 1 | A | Nantwich | 2-1 | Home game switched. County scratched before round 2 (A v Stalybridge Cel) due to fine for playing weak side in this game |
| 1912-13 | R | 1 | H | HOYLAKE | 3-0 | |
| R | 2 | H | LOSTOCK GRALAM | 0-1 | ||
| 1913-14 | R | 1 | H | TRANMERE ROVERS | 6-0 | |
| R | 2 | A | Sandbach Ramblers | 1-3 | ||
| 1914-15 | R | 1 | A | Congleton Town | 4-0 | Home game switched |
| R | 2 | H | HYDE | 8-1 | ||
| R | s | A | Altrincham | 3-1 | After extra time, full time 1-1 | |
| R | f | H | TRANMERE ROVERS | 1-0 | After extra time | |
| 1921-22 | R | 1 | A | Witton Albion | 2-2 | Home game switched |
| R | 1r | A | Witton Albion | 0-2 | ||
| 1922-23 | R | 1 | A | Tranmere Rovers Res | 4-0 | |
| R | 2 | H | SANDBACH RAMBLERS | 4-0 | ||
| R | 3 | A | Macclesfield | 1-7 | ||
| 1923-24 | R | 1 | A | Hyde United | 4-0 | Home game switched |
| R | 2 | A | Wallasey United | 3-0 | Home game switched | |
| R | 3 | A | Ellesmere Port Cement | 5-1 | ||
| R | s | A | Tranmere Rovers Res | 0-1 | ||
| 1924-25 | R | 1 | A | Moulton Alexandra | 5-1 | Away game switched |
| R | 2 | H | ALTRINCHAM | 3-1 | ||
| R | 3 | A | Runcorn | 0-2 | ||
| 1925-26 | R | 1 | H | HYDE UNITED | 5-2 | |
| R | 2 | A | Altrincham | 1-5 | ||
| 1926-27 | R | 1 | H | WIRRAL RAILWAY | 9-2 | |
| R | 2 | A | Witton Albion | 2-3 | ||
| 1927-28 | R | 1 | A | Winsford United | 2-1 | |
| R | 2 | H | TRANMERE ROVERS RES | 4-1 | ||
| R | 3 | A | Crewe Alexandra Res | 1-2 | ||
| 1928-29 | R | 1 | A | Altrincham | 1-2 | Home game switched |
| 1929-30 | R | 1 | H | CONGLETON TOWN | 5-2 | |
| R | 2 | A | Sandbach Ramblers | 2-3 | ||
| 1930-31 | R | 1 | A | Ellesmere Port Town | 6-3 | |
| R | 2 | H | WITTON ALBION | 4-1 | ||
| R | 3 | A | Crewe Alexandra Res | 1-3 | Home game switched | |
| 1931-32 | R | 1 | H | WINSFORD UNITED | 4-1 | |
| R | 2 | A | Witton Albion | 4-3 | ||
| R | 3 | A | Stalybridge Celtic | 3-1 | Home game switched | |
| R | s | N | Chester | 1-3 | At Moss Lane, Altrincham | |
| 1934-35 | R | 1 | A | Tranmere Rovers Res | 0-6 | |
| 1935-36 | R | 2 | A | Ellesmere Port Town | 1-0 | Home game switched |
| R | 3 | H | CONGLETON TOWN | 7-0 | ||
| R | s | N | Runcorn | 1-1 | At Gresty Road, Crewe Alex. After extra time |
|
| R | sr | N | Runcorn | 0-4 | At Drill Field, Northwich Vic | |
| 1936-37 | R | 2 | A | Heswall | 2-3 | |
| 1937-38 | R | 2 | A | Macclesfield | 1-3 | |
| 1938-39 | R | 2 | A | Winsford United | 2-2 | |
| R | 2r | H | WINSFORD UNITED | 2-0 | ||
| R | 3 | H | ALTRINCHAM | 2-2 | ||
| R | 3r | A | Altrincham | 4-0 | ||
| R | s | N | Runcorn | 2-1 | At North Western Ground, Winsford U | |
| R | f | N | Witton Albion | 0-3 | At Gresty Road, Crewe Alex | |
| 1939-40 | R | 2 | A | Hyde United | 2-7 | |
| 1945-46 | R | 2 | A | Hyde United | 0-3 | |
| 1946-47 | R | 2 | A | Hoylake Athletic | 2-2 | May have been switched to Edgeley Park |
| R | 2r | H | HOYLAKE ATHLETIC | 4-3 | ||
| R | 3 | A | Imperial Chemical Industries (Alkali) | 5-2 | ||
| R | s | N | Chester Res | 1-0 | At Rhyl, After extra time | |
| R | f | N | Hyde United | 1-0 | At Gresty Road, Crewe Alex | |
| 1947-48 | R | 1 | A | Runcorn | 4-7 | |
| 1948-49 | R | 1 | A | Macclesfield Town | 2-0 | |
| R | 2 | A | Witton Albion | 1-1 | Home game switched | |
| R | 2r | A | Witton Albion | 4-2 | ||
| R | s | N | Stalybridge Celtic | 3-1 | At Ewen Fields, Hyde U. After extra time, full time 1-1 |
|
| R | f | N | Winsford United | 2-0 | At Gresty Road, Crewe Alex. After extra time |
|
| 1949-50 | R | 1 | A | Altrincham | 0-2 | |
| 1950-51 | R | 1 | A | Winsford United | 3-0 | |
| R | 2 | H | ELLESMERE PORT TOWN | 1-0 | ||
| R | s | N | Northwich Victoria | 0-2 | At Winsford U, After extra time | |
| 1951-52 | R | 1 | A | Northwich Victoria | 3-2 | |
| R | 2 | A | Winsford United | 2-5 | ||
| 1952-53 | R | 1 | A | Congleton Town | 3-1 | |
| R | 2 | A | Winsford United | 2-2 | ||
| R | 2r | H | WINSFORD UNITED | 3-1 | After extra time | |
| R | s | N | Stalybridge Celtic | 0-2 | At Ewen Fields, Hyde U | |
| 1953-54 | R | 1 | H | RUNCORN | 0-0 | |
| R | 1r | A | Runcorn | 0-1 | ||
| 1954-55 | R | 1 | H | CREWE ALEXANDRA RES | 4-0 | |
| R | 2 | A | Congleton Town | 0-2 | ||
| 1955-56 | R | 1 | A | Runcorn | 1-0 | |
| R | 2 | H | WINSFORD UNITED | 4-3 | ||
| R | s | N | Witton Albion | 0-3 | At Drill Field, Northwich Vic | |
| 1956-57 | R | 1 | A | Congleton Town | 3-0 | |
| R | 2 | H | WINSFORD UNITED | 1-1 | ||
| R | 2r | A | Winsford United | 2-1 | ||
| R | s | N | Hyde United | 0-5 | At Stalybridge | |
| 1957-58 | R | 1 | A | Witton Albion | 2-1 | |
| R | 2 | A | Ellesmere Port Town | 1-1 | ||
| R | 2r | H | ELLESMERE PORT TOWN | 2-1 | ||
| R | s | N | Northwich Victoria | 4-2 | At Moss Lane, Altrincham. After extra time, full time 1-1 |
|
| R | f,1 | H | TRANMERE ROVERS RES | 2-0 | ||
| R | f,2 | A | Tranmere Rovers Res | 0-6 | ||
| 1965-66 | R | 1 | H | MACCLESFIELD TOWN | 2-2 | |
| R | 1r | A | Macclesfield Town | 2-0 | ||
| R | 2 | H | HYDE UNITED | 3-1 | ||
| R | s | N | Altrincham | 1-0 | At Stalybridge | |
| R | f | N | Northwich Victoria | 2-0 | At Moss Rose, Macclesfield T | |
| 1966-67 | R | 1 | H | HYDE UNITED | 1-2 | |
| 1967-68 | R | 1 | H | ALTRINCHAM | 1-1 | |
| R | 1r | A | Altrincham | 0-1 | ||
| 1968-69 | R | 1 | H | STALYBRIDGE CELTIC | 0-2 | |
| 1969-70 | R | 1 | A | New Brighton | 1-3 | |
| 1970-71 | R | 1 | H | TRANMERE ROVERS RES | 1-0 | |
| R | 2 | A | Hyde United | 0-3 | ||
| 1971-72 | R | 1 | H | RUNCORN | 2-1 | |
| R | 2 | A | Northwich Victoria | 0-4 | ||
| 1972-73 | R | 1 | A | Nantwich | 3-1 | |
| R | 2 | A | Altrincham | 0-2 | ||
| 1973-74 | R | 1 | A | Winsford United | 1-0 | Home game switched |
| R | 2 | H | NORTHWICH VICTORIA | 0-1 | ||
| 1974-75 | R | 1 | H | MACCLESFIELD TOWN | 0-2 | |
| 1975-76 | R | 1 | A | Altrincham | 0-1 | |
| 1976-77 | R | 1 | A | Middlewich Athletic | 2-0 | |
| R | 2 | A | Nantwich Town | 0-2 | ||
| 1977-78 | R | 1 | A | Northwich Victoria | 0-3 | |
| 1978-79 | R | 1 | A | Northwich Victoria | 1-4 | |
| 1979-80 | R | 1 | H | VAUXHALL GM | 4-0 | |
| R | 2 | H | WINSFORD UNITED | 0-0 | ||
| R | 2r | A | Winsford United | 0-1 | ||
| 1980-81 | R | 1 | H | RUNCORN | 0-2 | |
| 1981-82 | R | 1 | A | Vauxhall GM | 5-0 | |
| R | 2 | A | Macclesfield Town | 0-3 | ||
| 1982-83 | R | 1 | H | DUKINFIELD TOWN | 0-0 | Away game switched |
| R | 1r | H | DUKINFIELD TOWN | 2-2 | After extra time | |
| R | 1r2 | A | Dukinfield Town | 1-0 | ||
| R | 2 | A | Congleton Town | 1-1 | Home game switched | |
| R | 2r | A | Congleton Town | 0-2 | ||
| 1983-84 | R | 1 | A | Hyde United | 2-5 | Home game switched |
| 1984-85 | R | 1 | A | Hyde United | 0-8 | Home game switched |
| 2000-01 | R | 1 | A | Runcorn | 4-1 | |
| R | 2 | H | CREWE ALEXANDRA RES | 3-1 | ||
| R | s | A | Macclesfield Town Res | 8-5 | ||
| R | f | N | Stalybridge Celtic | 1-5 | At Ewen Fields, Hyde U | |
| 2001-02 | R | 1 | A | Nantwich Town | 3-1 | |
| R | 2 | H | CREWE ALEXANDRA RES | 1-6 | ||
| 2002-03 | R | 1 | A | Nantwich Town | 1-1 | After extra time |
| R | 1r | H | NANTWICH TOWN | 2-1 | ||
| R | 2 | H | CHESTER CITY | 1-3 | After extra time. Chester later expelled and County reinstated |
|
| R | s | H | NORTHWICH VICTORIA | 1-2 | ||
| 2003-04 | R | 1 | A | Woodley Sports | 0-1 | |
| 2004-05 | R | A | Alsager Town | 0-4 | Home game switched | |
| 2005-06 | R | 1 | A | Crewe Alexandra Res | 0-2 | |
| 2006-07 | R | 1 | A | Nantwich Town | 4-2 | |
| R | 2 | A | Northwich Victoria | 1-2 | ||
Details for non senior competitions may not be complete