Cup History - Chesterfield FC

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Cup history

Chesterfield

Matches where the winner was decided by a penalty shootout or the toss of a coin are currently recorded as a draw

F.A. Cup 1894-2008	Venue	Played	Won	Drawn	Lost	For	Against
	Home	98	44	21	33	157	134
	Away	98	21	25	52	115	173
	Neutral	4	1	1	2	5	7
	Total	200	66	47	87	277	314

League Cup 1960-2008	Venue	Played	Won	Drawn	Lost	For	Against
	Home	61	26	13	22	100	82
	Away	61	16	14	31	67	108
	Neutral	0	0	0	0	0	0
	Total	122	42	27	53	167	190

(Associate Members) 1983-2008	Venue	Played	Won	Drawn	Lost	For	Against
	Home	26	13	3	10	40	37
	Away	34	10	6	18	39	52
	Neutral	0	0	0	0	0	0
	Total	60	23	9	28	79	89

Click a season name to see the selected team's full cup performances or a cup name to view it's full results round by round

Season	Competition	Round Reached	Date	Home		Away

2007/2008	F.A. Cup	1st Round	Sat 10 Nov	Chesterfield	1 - 2	Tranmere Rvs.
	League Cup	1st Round	Tue 14 Aug	Sheff. Utd.	3 - 1	Chesterfield
	(Associate Members)	Northern Section 1st Round	Tue 04 Sep	Chesterfield	1 - 3	Hartlepool U.

2006/2007	F.A. Cup	1st Round	Sat 11 Nov	Chesterfield	0 - 1	Basingstoke T.
	League Cup	4th Round	Tue 07 Nov	Chesterfield	3 - 3	Charlton Ath.
after extra time, 90 minutes 2-2, Charlton Athletic won 4-3 on penalties
	(Associate Members)	Northern Section Semi-Final	Wed 10 Jan	Chesterfield	2 - 4	Crewe Alex.

2005/2006	F.A. Cup	1st Round Replay	Wed 16 Nov	Chesterfield	1 - 2	Leyton Orient
	League Cup	1st Round	Wed 24 Aug	Chesterfield	2 - 4	Huddersfield
	(Associate Members)	Northern Section 1st Round	Tue 18 Oct	Macclesfield	2 - 0	Chesterfield

2004/2005	F.A. Cup	1st Round	Sat 13 Nov	Scunthorpe U.	2 - 0	Chesterfield
	League Cup	1st Round	Tue 24 Aug	Rotherham U.	2 - 1	Chesterfield
	(Associate Members)	Northern Section 1st Round	Tue 28 Sep	Macclesfield	2 - 1	Chesterfield

2003/2004	F.A. Cup	1st Round	Sat 08 Nov	Tranmere Rvs.	3 - 2	Chesterfield
	League Cup	1st Round	Tue 12 Aug	Chesterfield	0 - 0	Burnley
after extra time, 90 minutes 0-0, Burnley won 3-2 on penalties
	(Associate Members)	Northern Section 2nd Round	Tue 04 Nov	Lincoln City	4 - 3	Chesterfield
after extra time, 90 minutes 3-3, Lincoln City won on silver goal rule

2002/2003	F.A. Cup	1st Round	Sat 16 Nov	Chesterfield	1 - 2	Morecambe
	League Cup	2nd Round	Tue 01 Oct	Chesterfield	1 - 1	West Ham Utd.
	(Associate Members)	Northern Section 2nd Round	Tue 12 Nov	Port Vale	1 - 1	Chesterfield
after extra time, 90 minutes 1-1, Port Vale won 4-3 on penalties

2001/2002	F.A. Cup	2nd Round Replay	Tue 18 Dec	Southend Utd.	2 - 0	Chesterfield
	League Cup	1st Round	Tue 21 Aug	Port Vale	2 - 1	Chesterfield
	(Associate Members)	Northern Section Quarter-Final	Tue 04 Dec	Chesterfield	0 - 3	Blackpool

2000/2001	F.A. Cup	1st Round	Sat 18 Nov	Chesterfield	0 - 1	Bristol City
	League Cup	2nd Round	Wed 27 Sep	Fulham	4 - 0	Chesterfield
	(Associate Members)	Northern Section Semi-Final	Tue 13 Feb	Lincoln City	4 - 1	Chesterfield

1999/2000	F.A. Cup	1st Round	Sat 30 Oct	Chesterfield	1 - 2	Enfield
	League Cup	2nd Round	Tue 21 Sep	Middlesbrough	2 - 1	Chesterfield
Middlesbrough won 2-1 on aggregate
	(Associate Members)	Northern Section Semi-Final	Tue 15 Feb	Chesterfield	0 - 1	Stoke City

1998/1999	F.A. Cup	1st Round	Sat 14 Nov	Wycombe Wdrs.	1 - 0	Chesterfield
	League Cup	2nd Round	Tue 22 Sep	Chesterfield	1 - 3	Leicester City
Leicester City won 6-1 on aggregate
	(Associate Members)	Northern Section Quarter-Final	Tue 19 Jan	Wrexham	3 - 2	Chesterfield

1997/1998	F.A. Cup	2nd Round Replay	Tue 16 Dec	Chesterfield	0 - 2	Grimsby Town
	League Cup	2nd Round	Tue 30 Sep	Barnsley	4 - 1	Chesterfield
Barnsley won 6-2 on aggregate
	(Associate Members)	Northern Section 1st Round	Tue 09 Dec	Chesterfield	0 - 1	Grimsby Town

1996/1997	F.A. Cup	Semi Final Replay	Tue 22 Apr	Middlesbrough	3 - 0	Chesterfield
played at Hillsbrough
	League Cup	1st Round	Tue 03 Sep	Chesterfield	1 - 2	Stockport Co.
Stockport County won 4-2 on aggregate
	(Associate Members)	Northern Section 1st Round	Mon 09 Dec	Chesterfield	0 - 2	Preston N.E.

1995/1996	F.A. Cup	2nd Round	Sat 02 Dec	Wrexham	3 - 2	Chesterfield
	League Cup	1st Round	Tue 05 Sep	Bury	2 - 1	Chesterfield
Bury won 3-1 on aggregate
	(Associate Members)	Northern Section Semi-Final	Tue 30 Jan	Carlisle Utd.	1 - 0	Chesterfield

1994/1995	F.A. Cup	1st Round Replay	Tue 22 Nov	Scarborough	2 - 0	Chesterfield
	League Cup	2nd Round	Tue 27 Sep	Wolves	1 - 1	Chesterfield
Wolverhampton Wanderers won 4-2 on aggregate
	(Associate Members)	Northern Section 1st Round	Tue 29 Nov	Carlisle Utd.	1 - 0	Chesterfield

1993/1994	F.A. Cup	1st Round	Sat 13 Nov	Chesterfield	0 - 1	Rochdale
	League Cup	2nd Round	Tue 05 Oct	Chesterfield	0 - 2	West Ham Utd.
West Ham United won 7-1 on aggregate
	(Associate Members)	Northern Section Preliminary Round Group Six	Tue 09 Nov	Chesterfield	1 - 2	Lincoln City

1992/1993	F.A. Cup	1st Round Replay	Wed 25 Nov	Chesterfield	2 - 2	Macclesfield
after extra time, 90 minutes ?-?, Macclesfield Town won 3-2 on penalties
	League Cup	2nd Round	Tue 06 Oct	Chesterfield	1 - 4	Liverpool
	(Associate Members)	Northern Section Semi-Final	Tue 23 Feb	Stockport Co.	2 - 1	Chesterfield

1991/1992	F.A. Cup	1st Round	Sat 16 Nov	Darlington	2 - 1	Chesterfield
	League Cup	1st Round	Tue 27 Aug	Chesterfield	1 - 2	Stoke City
Stoke City won 3-1 on aggregate
	(Associate Members)	Northern Section 1st Round	Tue 14 Jan	Bury	2 - 1	Chesterfield

1990/1991	F.A. Cup	2nd Round	Tue 11 Dec	Chesterfield	3 - 4	Bolton Wdrs.
	League Cup	1st Round	Tue 11 Sep	Hartlepool U.	2 - 2	Chesterfield
Hartlepool United won 4-3 on aggregate
	(Associate Members)	Northern Section Preliminary Round Group Five	Tue 18 Dec	Scunthorpe U.	3 - 1	Chesterfield

1989/1990	F.A. Cup	2nd Round	Sat 09 Dec	Chesterfield	0 - 2	Huddersfield
	League Cup	1st Round	Tue 29 Aug	Chesterfield	1 - 1	Birmingham C.
Birmingham City won 3-2 on aggregate
	(Associate Members)	Northern Section Preliminary Round Group Eight	Tue 12 Dec	Chesterfield	2 - 1	Halifax Town

1988/1989	F.A. Cup	1st Round Replay	Mon 28 Nov	Chesterfield	2 - 3	Bolton Wdrs.
	League Cup	1st Round	Tue 06 Sep	Chesterfield	1 - 1	Port Vale
Port Vale won 4-3 on aggregate
	(Associate Members)	Southern Section Quarter-Final	Tue 21 Feb	Chesterfield	0 - 1	Brentford

1987/1988	F.A. Cup	1st Round Replay	Tue 17 Nov	Chesterfield	0 - 1	Notts. County
	League Cup	1st Round	Wed 26 Aug	Peterborough	2 - 0	Chesterfield
Peterborough United won 3-2 on aggregate
	(Associate Members)	Northern Section 1st Round	Tue 19 Jan	Halifax Town	2 - 1	Chesterfield
after extra time, 90 minutes 1-1

1986/1987	F.A. Cup	1st Round	Sat 15 Nov	Walsall	2 - 0	Chesterfield
	League Cup	1st Round	Tue 02 Sep	Wrexham	2 - 2	Chesterfield
Wrexham won 4-2 on aggregate
	(Associate Members)	Northern Section 1st Round	Tue 27 Jan	Rochdale	3 - 0	Chesterfield

1985/1986	F.A. Cup	1st Round Replay	Tue 19 Nov	Chesterfield	0 - 1	Tranmere Rvs.
	League Cup	1st Round	Tue 03 Sep	Chesterfield	3 - 4	Bradford City
Bradford City won 6-5 on aggregate
	(Associate Members)	Northern Section Preliminary Round Group Five	Tue 21 Jan	Chesterfield	1 - 2	Burnley

1984/1985	F.A. Cup	2nd Round	Sat 08 Dec	Walsall	1 - 0	Chesterfield
	League Cup	1st Round	Tue 04 Sep	Chesterfield	1 - 2	Halifax Town
Halifax Town won 3-2 on aggregate
	(Associate Members)	Northern Section 2nd Round	Tue 12 Mar	York City	1 - 0	Chesterfield

1983/1984	F.A. Cup	2nd Round Replay	Mon 19 Dec	Burnley	3 - 2	Chesterfield
	League Cup	2nd Round	Wed 26 Oct	Everton	2 - 2	Chesterfield
Everton won 3-2 on aggregate
	(Associate Members)	Northern Section 1st Round	Tue 21 Feb	Scunthorpe U.	2 - 1	Chesterfield

1982/1983	F.A. Cup	1st Round Replay	Wed 24 Nov	Peterborough	2 - 1	Chesterfield
	League Cup	1st Round	Wed 15 Sep	Hartlepool U.	2 - 0	Chesterfield
Hartlepool United won 3-2 on aggregate

1981/1982	F.A. Cup	2nd Round	Sat 12 Dec	Chesterfield	0 - 1	Huddersfield
	League Cup	1st Round	Tue 15 Sep	Chesterfield	1 - 1	Doncaster Rvs.
aggregate 1-1, Chesterfield won on away goals rule

1980/1981	F.A. Cup	3rd Round Replay	Tue 06 Jan	Chesterfield	1 - 2	Peterborough
	League Cup	2nd Round	Wed 03 Sep	Oxford Utd.	3 - 0	Chesterfield
Oxford United won 4-3 on aggregate

1979/1980	F.A. Cup	1st Round Replay	Tue 27 Nov	Chesterfield	2 - 3	Grimsby Town
	League Cup	3rd Round	Tue 25 Sep	Liverpool	3 - 1	Chesterfield

1978/1979	F.A. Cup	1st Round Replay	Wed 06 Dec	Chesterfield	0 - 1	Darlington
	League Cup	3rd Round	Wed 04 Oct	Chesterfield	4 - 5	Charlton Ath.

1977/1978	F.A. Cup	2nd Round	Sat 17 Dec	Blyth	1 - 0	Chesterfield
	League Cup	2nd Round	Wed 31 Aug	Chesterfield	0 - 1	Man. City

1976/1977	F.A. Cup	2nd Round 2nd Replay	Tue 21 Dec	Walsall	1 - 0	Chesterfield
played at neutral ground
	League Cup	1st Round	Tue 17 Aug	Rotherham U.	3 - 0	Chesterfield
Rotherham United won 4-3 on aggregate

1975/1976	F.A. Cup	1st Round	Sat 22 Nov	Bradford City	1 - 0	Chesterfield
	League Cup	1st Round	Mon 25 Aug	Chesterfield	3 - 2	Lincoln City
Lincoln City won 6-5 on aggregate

1974/1975	F.A. Cup	3rd Round	Sat 04 Jan	Sunderland	2 - 0	Chesterfield
	League Cup	2nd Round	Tue 10 Sep	Sheff. Utd.	3 - 1	Chesterfield

1973/1974	F.A. Cup	1st Round Replay	Wed 28 Nov	Barnsley	2 - 1	Chesterfield
	League Cup	3rd Round	Tue 30 Oct	Southampton	3 - 0	Chesterfield

1972/1973	F.A. Cup	2nd Round Replay	Wed 13 Dec	Chesterfield	0 - 1	Grimsby Town
	League Cup	3rd Round	Tue 03 Oct	Millwall	2 - 0	Chesterfield

1971/1972	F.A. Cup	3rd Round	Sat 15 Jan	Stoke City	2 - 1	Chesterfield
	League Cup	2nd Round	Wed 08 Sep	Chesterfield	2 - 3	Aston Villa

1970/1971	F.A. Cup	2nd Round Replay	Wed 16 Dec	Workington	3 - 2	Chesterfield
	League Cup	1st Round	Wed 19 Aug	Mansfield Town	6 - 2	Chesterfield

1969/1970	F.A. Cup	1st Round	Sat 15 Nov	Tranmere Rvs.	3 - 0	Chesterfield
	League Cup	1st Round Replay	Wed 20 Aug	Chesterfield	0 - 1	Bradford City

1968/1969	F.A. Cup	3rd Round	Sat 04 Jan	Portsmouth	3 - 0	Chesterfield
	League Cup	1st Round	Tue 13 Aug	Derby County	3 - 0	Chesterfield

1967/1968	F.A. Cup	3rd Round	Sat 27 Jan	Blackpool	2 - 1	Chesterfield
	League Cup	1st Round	Wed 23 Aug	Grimsby Town	1 - 0	Chesterfield

1966/1967	F.A. Cup	1st Round	Sat 26 Nov	Wrexham	3 - 2	Chesterfield
	League Cup	2nd Round	Tue 13 Sep	York City	3 - 2	Chesterfield

1965/1966	F.A. Cup	1st Round	Sat 13 Nov	Chesterfield	0 - 2	Chester
	League Cup	3rd Round Replay	Wed 20 Oct	Stoke City	2 - 1	Chesterfield

1964/1965	F.A. Cup	3rd Round	Sat 09 Jan	Chesterfield	0 - 3	Peterborough
	League Cup	4th Round	Wed 04 Nov	Northampton	4 - 1	Chesterfield

1963/1964	F.A. Cup	3rd Round	Sat 04 Jan	Oxford Utd.	1 - 0	Chesterfield
	League Cup	1st Round	Wed 04 Sep	Chesterfield	0 - 1	Halifax Town

1962/1963	F.A. Cup	2nd Round	Sat 24 Nov	Barnsley	2 - 1	Chesterfield
	League Cup	1st Round	Wed 05 Sep	Darlington	1 - 0	Chesterfield

1961/1962	F.A. Cup	2nd Round Replay	Wed 29 Nov	Oldham Ath.	4 - 2	Chesterfield
after extra time, 90 minutes ?-?
	League Cup	1st Round	Wed 13 Sep	Chesterfield	2 - 3	Norwich City

1960/1961	F.A. Cup	3rd Round Replay	Wed 11 Jan	Blackburn R.	3 - 0	Chesterfield
	League Cup	3rd Round	Wed 23 Nov	Chesterfield	0 - 4	Leeds Utd.

1959/1960	F.A. Cup	1st Round	Sat 14 Nov	South Shields	2 - 1	Chesterfield

1958/1959	F.A. Cup	3rd Round	Sat 10 Jan	Colchester U.	2 - 0	Chesterfield

1957/1958	F.A. Cup	1st Round	Sat 16 Nov	York City	1 - 0	Chesterfield

1956/1957	F.A. Cup	3rd Round	Sat 05 Jan	Burnley	7 - 0	Chesterfield

1955/1956	F.A. Cup	2nd Round	Sat 10 Dec	Chesterfield	1 - 2	Hartlepools

1954/1955	F.A. Cup	1st Round	Sat 20 Nov	Hartlepools	1 - 0	Chesterfield

1953/1954	F.A. Cup	4th Round Replay	Wed 03 Feb	Chesterfield	2 - 4	Sheff. Wed.

1952/1953	F.A. Cup	2nd Round Replay	Wed 10 Dec	Chesterfield	2 - 4	Shrewsbury Tn.

1951/1952	F.A. Cup	2nd Round	Sat 15 Dec	Norwich City	3 - 1	Chesterfield

1950/1951	F.A. Cup	3rd Round	Sat 06 Jan	Brighton & HA	2 - 1	Chesterfield

1949/1950	F.A. Cup	5th Round Replay	Wed 15 Feb	Chelsea	3 - 0	Chesterfield

1948/1949	F.A. Cup	3rd Round	Sat 08 Jan	Wolves	6 - 0	Chesterfield

1947/1948	F.A. Cup	3rd Round	Sat 10 Jan	Derby County	2 - 0	Chesterfield

1946/1947	F.A. Cup	4th Round	Sat 25 Jan	Middlesbrough	2 - 1	Chesterfield

1945/1946	F.A. Cup	3rd Round	Wed 09 Jan	York City	3 - 2	Chesterfield
after extra time, 90 minutes ?-?, York City won 4-3 on aggregate

1938/1939	F.A. Cup	3rd Round Replay	Mon 16 Jan	Southend Utd.	4 - 3	Chesterfield

1937/1938	F.A. Cup	5th Round Replay	Wed 16 Feb	Tottenham H.	2 - 1	Chesterfield

1936/1937	F.A. Cup	3rd Round	Sat 16 Jan	Chesterfield	1 - 5	Arsenal

1935/1936	F.A. Cup	2nd Round Replay	Thu 19 Dec	Walsall	2 - 1	Chesterfield

1934/1935	F.A. Cup	3rd Round	Sat 12 Jan	Swindon Town	2 - 1	Chesterfield

1933/1934	F.A. Cup	3rd Round Replay	Wed 17 Jan	Aston Villa	2 - 0	Chesterfield

1932/1933	F.A. Cup	5th Round	Sat 18 Feb	Burnley	1 - 0	Chesterfield

1931/1932	F.A. Cup	4th Round	Sat 23 Jan	Chesterfield	2 - 4	Liverpool

1930/1931	F.A. Cup	1st Round	Sat 29 Nov	Chesterfield	1 - 2	Notts. County

1929/1930	F.A. Cup	3rd Round Replay	Wed 15 Jan	Middlesbrough	4 - 3	Chesterfield

1928/1929	F.A. Cup	3rd Round	Sat 12 Jan	Chesterfield	1 - 7	Huddersfield

1927/1928	F.A. Cup	1st Round	Sat 26 Nov	Darlington	4 - 1	Chesterfield

1926/1927	F.A. Cup	3rd Round	Sat 08 Jan	Fulham	4 - 3	Chesterfield

1925/1926	F.A. Cup	3rd Round	Sat 09 Jan	Chesterfield	0 - 1	Clapton Orient

1913/1914	F.A. Cup	1st Round	Sat 10 Jan	West Ham Utd.	8 - 1	Chesterfield

1912/1913	F.A. Cup	1st Round	Sat 18 Jan	Chesterfield	1 - 4	Nottm. Forest

1910/1911	F.A. Cup	2nd Round	Sat 04 Feb	Chelsea	4 - 1	Chesterfield

1909/1910	F.A. Cup	1st Round Replay	Wed 19 Jan	Fulham	2 - 1	Chesterfield

1908/1909	F.A. Cup	1st Round	Sat 16 Jan	Chesterfield	0 - 2	Glossop N. E.

1907/1908	F.A. Cup	2nd Round	Sat 01 Feb	Bristol Rvs.	2 - 0	Chesterfield

1906/1907	F.A. Cup	1st Round Replay	Mon 21 Jan	Chesterfield	0 - 4	Derby County
replayed after initial abandoned game 16/01 (1-1)

1905/1906	F.A. Cup	2nd Round	Sat 03 Feb	Everton	3 - 0	Chesterfield

1900/1901	F.A. Cup	1st Round Replay	Wed 13 Feb	Chesterfield	1 - 2