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The website of Stockport County's Historical Advisors
| Season | Lev | Rnd | Ven & Opponents | Res | Notes | |
| 1893-94 | F | 1 | H | BURTON WANDERERS | 0-1 | |
| 1905-06 | F | 1 | A | Lincoln City | 2-4 | |
| 1906-07 | F | 1 | A | Fulham | 0-0 | Home advantage sold |
| F | 1r | A | Fulham | 1-2 | ||
| 1907-08 | F | 1 | A | Aston Villa | 0-3 | Home advantage sold |
| 1908-09 | F | 1 | A | Grimsby Town | 2-0 | Abandoned after 75 minutes |
| F | 1 | A | Grimsby Town | 2-0 | ||
| F | 2 | H | GLOSSOP | 1-1 | ||
| F | 2r | A | Glossop | 0-1 | After extra time | |
| 1909-10 | F | 1 | H | BOLTON WANDERERS | 4-1 | |
| F | 2 | H | LEYTON | 0-2 | ||
| 1911-12 | F | 1 | A | Lincoln City | 0-2 | |
| 1912-13 | F | 1 | A | Everton | 1-1 | Abandoned after 48 minutes |
| F | 1 | A | Everton | 1-5 | ||
| 1914-15 | F | 1 | A | Liverpool | 0-3 | |
| 1919-20 | F | 1 | A | Preston North End | 1-3 | |
| 1920-21 | F | 1 | A | Everton | 0-1 | |
| 1924-25 | F | 1 | A | Queens Park Rangers | 3-1 | |
| F | 2 | A | Birmingham | 0-1 | ||
| 1925-26 | F | 3 | A | Sheffield United | 0-2 | |
| 1926-27 | F | 1 | A | Nelson | 1-4 | |
| 1927-28 | F | 1 | H | OSWESTRY TOWN [wal] | 5-2 | |
| F | 2 | A | Crewe Alexandra | 0-2 | ||
| 1928-29 | F | 1 | H | HALIFAX TOWN | 1-0 | |
| F | 2 | H | SOUTHPORT | 3-0 | ||
| F | 3 | A | Bradford City | 0-2 | ||
| 1929-30 | F | 1 | A | Wellington Town | 4-1 | |
| F | 2 | H | BARROW | 4-0 | ||
| F | 3 | A | Blackpool | 1-2 | ||
| 1930-31 | F | 1 | A | Hartlepools United | 3-2 | |
| F | 2 | A | Bristol Rovers | 2-4 | ||
| 1931-32 | F | 1 | A | Crook Town | 1-3 | |
| 1932-33 | F | 1 | A | Rochdale | 2-0 | |
| F | 2 | H | LUTON TOWN | 2-3 | ||
| 1933-34 | F | 1 | A | Lancaster Town | 1-0 | |
| F | 2 | H | CRYSTAL PALACE | 1-2 | ||
| 1934-35 | F | 1 | A | Blyth Spartans | 1-1 | |
| F | 1r | H | BLYTH SPARTANS | 4-1 | ||
| F | 2 | H | DARLINGTON | 3-2 | ||
| F | 3 | A | West Ham United | 1-1 | ||
| F | 3r | H | WEST HAM UNITED | 1-0 | ||
| F | 4 | A | Bradford City | 0-0 | ||
| F | 4r | H | BRADFORD CITY | 3-2 | After extra time, full time 2-2 | |
| F | 5 | H | WEST BROMWICH ALBION | 0-5 | ||
| 1935-36 | F | 3 | H | PLYMOUTH ARGYLE | 2-3 | |
| 1936-37 | F | 1 | A | Carlisle United | 1-2 | |
| 1937-38 | F | 3 | A | Middlesbrough | 0-2 | |
| 1938-39 | F | 1 | A | North Shields | 4-1 | |
| F | 2 | H | WALTHAMSTOW AVENUE | 0-0 | ||
| F | 2r | A | Walthamstow Avenue | 3-1 | ||
| F | 3 | A | Barnsley | 2-1 | ||
| F | 4 | A | Liverpool | 1-5 | ||
| 1945-46 | F | 1,1 | H | ROCHDALE | 1-2 | |
| F | 1,2 | A | Rochdale | 1-1 | ||
| 1946-47 | F | 1 | H | SOUTHPORT | 2-0 | |
| F | 2 | A | Halifax Town | 1-1 | ||
| F | 2r | H | HALIFAX TOWN | 2-1 | ||
| F | 3 | A | Bolton Wanderers | 1-5 | ||
| 1947-48 | F | 1 | H | ACCRINGTON STANLEY | 3-1 | |
| F | 2 | H | SHREWSBURY TOWN | 1-1 | Abandoned after 112 minutes | |
| F | 2r | A | Shrewsbury Town | 2-2 | After extra time | |
| F | 2r2 | N | Shrewsbury Town | 3-2 | At Maine Road, Manchester C. After extra time. |
|
| F | 3 | H | TORQUAY UNITED | 3-0 | ||
| F | 4 | A | Charlton Athletic | 0-3 | ||
| 1948-49 | F | 1 | A | Workington | 3-0 | |
| F | 2 | A | Scunthorpe United | 1-0 | ||
| F | 3 | A | Portsmouth | 0-7 | ||
| 1949-50 | F | 1 | H | BILLINGHAM SYNTHONIA | 3-0 | |
| F | 2 | A | Nottingham Forest | 2-0 | ||
| F | 3 | H | BARNSLEY | 4-2 | ||
| F | 4 | H | HULL CITY | 0-0 | ||
| F | 4r | A | Hull City | 2-0 | ||
| F | 5 | H | LIVERPOOL | 1-2 | ||
| 1950-51 | F | 3 | H | BRENTFORD | 2-1 | Exempt until this round |
| F | 4 | A | Blackpool | 1-2 | ||
| 1951-52 | F | 1 | H | GATESHEAD | 2-2 | After extra time |
| F | 1r | A | Gateshead | 1-1 | After extra time | |
| F | 1r2 | N | Gateshead | 1-2 | At Hillsborough, Sheffield Wed | |
| 1952-53 | F | 1 | A | North Shields | 6-3 | |
| F | 2 | H | GILLINGHAM | 3-1 | ||
| F | 3 | A | Walthamstow Avenue | 1-2 | ||
| 1953-54 | F | 1 | H | CHESTER | 4-2 | |
| F | 2 | H | WORKINGTON | 2-1 | ||
| F | 3 | H | HEADINGTON UNITED | 0-0 | ||
| F | 3r | A | Headington United | 0-1 | ||
| 1954-55 | F | 1 | H | CARLISLE UNITED | 0-1 | |
| 1955-56 | F | 1 | A | Mansfield Town | 0-2 | |
| 1956-57 | F | 1 | A | New Brighton | 3-3 | |
| F | 1r | H | NEW BRIGHTON | 2-3 | ||
| 1957-58 | F | 1 | H | BARROW | 2-1 | |
| F | 2 | H | HARTLEPOOLS UNITED | 2-1 | ||
| F | 3 | H | LUTON TOWN | 3-0 | ||
| F | 4 | A | West Ham United | 2-3 | ||
| 1958-59 | F | 1 | A | Hull City | 1-0 | |
| F | 2 | A | Blyth Spartans | 4-3 | ||
| F | 3 | H | BURNLEY | 1-3 | ||
| 1959-60 | F | 1 | A | West Auckland Town | 6-2 | |
| F | 2 | H | CREWE ALEXANDRA | 0-0 | ||
| F | 2r | A | Crewe Alexandra | 0-2 | ||
| 1960-61 | F | 1 | H | WORKINGTON | 1-0 | |
| F | 2 | H | BISHOP AUCKLAND | 2-0 | ||
| F | 3 | H | SOUTHPORT | 3-1 | ||
| F | 4 | A | Newcastle United | 0-4 | ||
| 1961-62 | F | 1 | H | ACCRINGTON STANLEY | 0-1 | |
| 1962-63 | F | 1 | A | Chesterfield | 1-4 | |
| 1963-64 | F | 1 | A | Barnsley | 0-1 | |
| 1964-65 | F | 1 | H | WIGAN ATHLETIC | 2-1 | |
| F | 2 | H | GRIMSBY TOWN | 0-0 | Abandoned after 58 minutes | |
| F | 2 | H | GRIMSBY TOWN | 1-0 | ||
| F | 3 | A | Bristol Rovers | 0-0 | ||
| F | 3r | H | BRISTOL ROVERS | 3-2 | ||
| F | 4 | A | Liverpool | 1-1 | ||
| F | 4r | H | LIVERPOOL | 0-2 | ||
| 1965-66 | F | 1 | A | Tranmere Rovers | 1-0 | |
| F | 2 | A | Southport | 3-3 | ||
| F | 2r | H | SOUTHPORT | 0-2 | ||
| 1966-67 | F | 1 | A | Darlington | 0-0 | |
| F | 1r | H | DARLINGTON | 1-1 | After extra time | |
| F | 1r2 | N | Darlington | 2-4 | At Elland Road, Leeds U | |
| 1967-68 | F | 1 | H | MACCLESFIELD TOWN | 1-1 | |
| F | 1r | A | Macclesfield Town | 1-2 | ||
| 1968-69 | F | 1 | H | BRADFORD (PARK AVENUE) | 3-0 | |
| F | 2 | H | BARROW | 2-0 | ||
| F | 3 | A | Blackburn Rovers | 0-2 | ||
| 1969-70 | F | 1 | H | MOSSLEY | 1-1 | |
| F | 1r | A | Mossley | 1-0 | ||
| F | 2 | H | SCUNTHORPE UNITED | 0-0 | ||
| F | 2r | A | Scunthorpe United | 0-4 | ||
| 1970-71 | F | 1 | A | Grantham | 1-2 | |
| 1971-72 | F | 1 | A | Doncaster Rovers | 2-1 | |
| F | 2 | A | Blyth Spartans | 0-1 | ||
| 1972-73 | F | 1 | H | WORKINGTON | 1-0 | |
| F | 2 | A | Rotherham United | 1-0 | ||
| F | 3 | H | HULL CITY | 0-0 | ||
| F | 3r | A | Hull City | 0-2 | After extra time | |
| 1973-74 | F | 1 | H | PORT VALE | 0-1 | |
| 1974-75 | F | 1 | H | STAFFORD RANGERS | 0-0 | |
| F | 1r | A | Stafford Rangers | 0-1 | ||
| 1975-76 | F | 1 | A | Hartlepool | 0-3 | |
| 1976-77 | F | 1 | A | Sheffield Wednesday | 0-2 | |
| 1977-78 | F | 1 | H | SCUNTHORPE UNITED | 3-0 | |
| F | 2 | A | Shrewsbury Town | 1-1 | ||
| F | 2r | H | SHREWSBURY TOWN | 1-2 | ||
| 1978-79 | F | 1 | H | MORECAMBE | 5-1 | |
| F | 2 | H | BRADFORD CITY | 4-2 | ||
| F | 3 | A | Wrexham [wal] | 2-6 | ||
| 1979-80 | F | 1 | A | Walsall | 0-2 | |
| 1980-81 | F | 1 | H | SHEFFIELD UNITED | 0-0 | |
| F | 1r | A | Sheffield United | 2-3 | After extra time | |
| 1981-82 | F | 1 | H | MOSSLEY | 3-1 | |
| F | 2 | A | Port Vale | 1-4 | ||
| 1982-83 | F | 1 | A | Mansfield Town | 2-3 | |
| 1983-84 | F | 1 | A | Telford United | 0-3 | |
| 1984-85 | F | 1 | H | WALSALL | 1-2 | |
| 1985-86 | F | 1 | H | TELFORD UNITED | 0-1 | |
| 1986-87 | F | 1 | A | Caernarfon Town [wal] | 0-1 | |
| 1987-88 | F | 1 | A | Telford United | 1-1 | |
| F | 1r | H | TELFORD UNITED | 2-0 | ||
| F | 2 | A | Runcorn | 1-0 | ||
| F | 3 | H | LEYTON ORIENT | 1-2 | ||
| 1988-89 | F | 1 | A | Scarborough | 1-2 | |
| 1989-90 | F | 1 | A | Burnley | 1-1 | |
| F | 1r | H | BURNLEY | 1-2 | ||
| 1990-91 | F | 1 | A | Rotherham United | 0-1 | |
| 1991-92 | F | 1 | H | LINCOLN CITY | 3-1 | |
| F | 2 | A | Wigan Athletic | 0-2 | ||
| 1992-93 | F | 1 | A | York City | 3-1 | |
| F | 2 | A | Macclesfield Town | 2-0 | ||
| F | 3 | A | Derby County | 1-2 | ||
| 1993-94 | F | 1 | A | Rotherham United | 2-1 | |
| F | 2 | H | HALIFAX TOWN | 5-1 | ||
| F | 3 | H | QUEENS PARK RANGERS | 2-1 | ||
| F | 4 | H | BRISTOL CITY | 0-4 | ||
| 1994-95 | F | 1 | A | Wrexham [wal] | 0-1 | |
| 1995-96 | F | 1 | H | LINCOLN CITY | 5-0 | |
| F | 2 | H | BLYTH SPARTANS | 2-0 | ||
| F | 3 | A | Everton | 2-2 | ||
| F | 3r | H | EVERTON | 2-3 | ||
| 1996-97 | F | 1 | H | DONCASTER ROVERS | 2-1 | |
| F | 2 | A | Mansfield Town | 3-0 | ||
| F | 3 | A | Stoke City | 2-0 | ||
| F | 4 | A | Birmingham City | 1-3 | ||
| 1997-98 | F | 3 | A | Preston North End | 2-1 | |
| F | 4 | A | Birmingham City | 1-2 | ||
| 1998-99 | F | 3 | A | Bury | 3-0 | |
| F | 4 | A | Sheffield Wednesday | 0-2 | ||
| 1999-00 | F | 3 | A | Grimsby Town | 2-3 | |
| 2000-01 | F | 3 | A | Preston North End | 1-0 | |
| F | 4 | A | Crewe Alexandra | 1-0 | ||
| F | 5 | A | Tottenham Hotspur | 0-4 | ||
| 2001-02 | F | 3 | H | BOLTON WANDERERS | 1-4 | |
| 2002-03 | F | 1 | H | SAINT ALBANS CITY | 4-1 | |
| F | 2 | H | PLYMOUTH ARGYLE | 0-3 | ||
| 2003-04 | F | 1 | A | Stevenage Borough | 1-2 | |
| 2004-05 | F | 1 | H | HUDDERSFIELD TOWN | 3-1 | |
| F | 2 | H | SWANSEA CITY [wal] | 0-0 | ||
| F | 2r | A | Swansea City [wal] | 1-2 | ||
| 2005-06 | F | 1 | H | SWANSEA CITY [wal] | 2-0 | |
| F | 2 | A | Hereford United | 2-0 | ||
| F | 3 | H | BRENTFORD | 2-3 | ||
| 2006-07 | F | 1 | A | Exeter City | 2-1 | |
| F | 2 | H | WYCOMBE WANDERERS | 2-1 | ||
| F | 3 | A | Watford | 1-4 | ||
| 2007-08 | F | 1 | H | STAINES TOWN | 1-1 | |
| F | 1r | A | Staines Town | 1-1 | After extra time, lost 3-4 on penalties | |
| 2008-09 | F | 1 | A | Yeovil Town | 1-1 | |
| F | 1r | H | YEOVIL TOWN | 5-0 | ||
| F | 2 | A | Gillingham | 0-0 | ||
| F | 2r | H | GILLINGHAM | 1-2 | ||
| 2009-10 | F | 1 | H | TOOTING AND MITCHAM UNITED | 5-0 | |
| F | 2 | N | Torquay United | 0-4 | Home game switched to Moss Lane, Macclesfield due to pitch repairs | |
| 2010-11 | F | 1 | H | PETERBOROUGH UNITED | 1-1 | |
| F | 1,r | A | Peterborough United | 1-4 | ||