| Season | Competition |
Round Reached | Date |
Home | |
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| 2007/2008 | F.A. Cup | 2nd Round | Sat 01 Dec | Hereford Utd. | 2 - 0 | Hartlepool U. |
| League Cup | 2nd Round | Tue 28 Aug | Sheff. Wed. | 2 - 1 | Hartlepool U. |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Northern Section Quarter-Final | Tue 13 Nov | Hartlepool U. | 1 - 1 | Morecambe |
| after extra time, 90 minutes 1-1, Morecambe won 4-2 on penalties |
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| 2006/2007 | F.A. Cup | 2nd Round | Sat 02 Dec | Macclesfield | 2 - 1 | Hartlepool U. |
| League Cup | 2nd Round | Tue 19 Sep | Hull City | 0 - 0 | Hartlepool U. |
| after extra time, 90 minutes 0-0, Hull City won 3-2 on penalties |
| (Associate Members) | Northern Section 2nd Round | Tue 31 Oct | Hartlepool U. | 1 - 3 | Doncaster Rvs. |
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| 2005/2006 | F.A. Cup | 2nd Round | Sat 03 Dec | Hartlepool U. | 1 - 2 | Tamworth |
| League Cup | 2nd Round | Tue 20 Sep | Charlton Ath. | 3 - 1 | Hartlepool U. |
| (Associate Members) | Northern Section 1st Round | Tue 18 Oct | Scunthorpe U. | 1 - 0 | Hartlepool U. |
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| 2004/2005 | F.A. Cup | 4th Round Replay | Sat 12 Feb | Hartlepool U. | 0 - 1 | Brentford |
| League Cup | 2nd Round | Tue 21 Sep | Crystal Palace | 2 - 1 | Hartlepool U. |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Northern Section Quarter-Final | Tue 30 Nov | Oldham Ath. | 3 - 1 | Hartlepool U. |
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| 2003/2004 | F.A. Cup | 3rd Round | Sat 03 Jan | Sunderland | 1 - 0 | Hartlepool U. |
| League Cup | 2nd Round | Tue 23 Sep | Hartlepool U. | 1 - 2 | West Brom. |
| (Associate Members) | Northern Section 1st Round | Tue 14 Oct | Oldham Ath. | 3 - 3 | Hartlepool U. |
| after extra time, 90 minutes 3-3, Oldham Athletiic won 5-3 on penalties |
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| 2002/2003 | F.A. Cup | 1st Round Replay | Tue 26 Nov | Hartlepool U. | 1 - 2 | Southend Utd. |
| League Cup | 1st Round | Tue 10 Sep | Hartlepool U. | 1 - 2 | Tranmere Rvs. |
| (Associate Members) | Northern Section 1st Round | Tue 22 Oct | Tranmere Rvs. | 5 - 0 | Hartlepool U. |
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| 2001/2002 | F.A. Cup | 1st Round | Sat 17 Nov | Swindon Town | 3 - 1 | Hartlepool U. |
| League Cup | 1st Round | Mon 20 Aug | Hartlepool U. | 0 - 2 | Nottm. Forest |
| (Associate Members) | Northern Section 1st Round | Tue 16 Oct | Hartlepool U. | 0 - 1 | Bury |
| after extra time, 90 minutes 0-0, Bury won on the golden goal rule |
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| 2000/2001 | F.A. Cup | 1st Round | Sat 18 Nov | Scunthorpe U. | 3 - 1 | Hartlepool U. |
| League Cup | 1st Round | Tue 05 Sep | Hartlepool U. | 3 - 2 | Burnley |
| (Associate Members) | Northern Section Quarter-Final | Tue 30 Jan | Lincoln City | 1 - 0 | Hartlepool U. |
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| 1999/2000 | F.A. Cup | 2nd Round | Sun 21 Nov | Hereford Utd. | 1 - 0 | Hartlepool U. |
| League Cup | 1st Round | Tue 24 Aug | Crewe Alex. | 1 - 0 | Hartlepool U. |
| Crewe Alexandra won 4-3 on aggregate |
| (Associate Members) | Northern Section Quarter-Final | Tue 22 Feb | Hartlepool U. | 1 - 2 | Carlisle Utd. |
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| 1998/1999 | F.A. Cup | 2nd Round | Sat 05 Dec | Fulham | 4 - 2 | Hartlepool U. |
| League Cup | 1st Round | Tue 18 Aug | Hartlepool U. | 0 - 3 | Bolton Wdrs. |
| Bolton Wanderers won 4-0 on aggregate |
| (Associate Members) | Northern Section Quarter-Final | Tue 26 Jan | Hartlepool U. | 0 - 3 | Lincoln City |
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| 1997/1998 | F.A. Cup | 1st Round | Sat 15 Nov | Hartlepool U. | 2 - 4 | Macclesfield |
| League Cup | 1st Round | Tue 26 Aug | Hartlepool U. | 2 - 1 | Tranmere Rvs. |
| Tranmere Rovers won 4-3 on aggregate |
| (Associate Members) | Northern Section 2nd Round | Tue 06 Jan | Hartlepool U. | 1 - 2 | Scunthorpe U. |
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| 1996/1997 | F.A. Cup | 1st Round Replay | Tue 26 Nov | York City | 3 - 0 | Hartlepool U. |
| League Cup | 1st Round | Tue 03 Sep | Lincoln City | 3 - 2 | Hartlepool U. |
| Lincoln City won 5-4 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 10 Dec | Hartlepool U. | 0 - 2 | Burnley |
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| 1995/1996 | F.A. Cup | 1st Round | Sat 11 Nov | Hartlepool U. | 2 - 4 | Darlington |
| League Cup | 2nd Round | Tue 03 Oct | Arsenal | 5 - 0 | Hartlepool U. |
| Arsenal won 8-0 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group One | Tue 07 Nov | Hartlepool U. | 3 - 2 | Blackpool |
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| 1994/1995 | F.A. Cup | 1st Round | Sat 12 Nov | Port Vale | 6 - 0 | Hartlepool U. |
| League Cup | 2nd Round | Wed 05 Oct | Arsenal | 2 - 0 | Hartlepool U. |
| Arsenal won 7-0 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group One | Tue 08 Nov | Hartlepool U. | 0 - 2 | Darlington |
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| 1993/1994 | F.A. Cup | 1st Round | Sat 13 Nov | Macclesfield | 2 - 0 | Hartlepool U. |
| League Cup | 2nd Round | Tue 05 Oct | Hartlepool U. | 0 - 2 | Grimsby Town |
| Grimsby Town won 5-0 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Four | Tue 09 Nov | York City | 2 - 0 | Hartlepool U. |
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| 1992/1993 | F.A. Cup | 4th Round | Sat 23 Jan | Sheff. Utd. | 1 - 0 | Hartlepool U. |
| League Cup | 2nd Round | Tue 06 Oct | Hartlepool U. | 2 - 2 | Sheff. Wed. |
| (Associate Members) | Northern Section 1st Round | Tue 12 Jan | Stockport Co. | 1 - 0 | Hartlepool U. |
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| 1991/1992 | F.A. Cup | 3rd Round Replay | Wed 15 Jan | Hartlepool U. | 0 - 2 | Ipswich Town |
| League Cup | 2nd Round | Tue 08 Oct | Crystal Palace | 6 - 1 | Hartlepool U. |
| Crystal Palace won 7-2 on aggregate |
| (Associate Members) | Northern Section Quarter-Final | Tue 04 Feb | Stockport Co. | 3 - 0 | Hartlepool U. |
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| 1990/1991 | F.A. Cup | 2nd Round | Sat 08 Dec | Wigan Ath. | 2 - 0 | Hartlepool U. |
| League Cup | 2nd Round | Tue 09 Oct | Hartlepool U. | 1 - 2 | Tottenham H. |
| Tottenham Hotspur won 7-1 on aggregate |
| (Associate Members) | Northern Section 1st Round | Tue 22 Jan | Bradford City | 3 - 2 | Hartlepool U. |
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| 1989/1990 | F.A. Cup | 1st Round | Sat 18 Nov | Hartlepool U. | 0 - 2 | Huddersfield |
| League Cup | 1st Round | Tue 29 Aug | York City | 4 - 1 | Hartlepool U. |
| York City won 7-4 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Six | Tue 28 Nov | Hartlepool U. | 1 - 4 | Rotherham U. |
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| 1988/1989 | F.A. Cup | 4th Round Replay | Tue 31 Jan | Bournemouth | 5 - 2 | Hartlepool U. |
| League Cup | 1st Round | Tue 06 Sep | Sheff. Utd. | 2 - 0 | Hartlepool U. |
| Sheffield United won 4-2 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Four | Tue 13 Dec | Hartlepool U. | 0 - 2 | York City |
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| 1987/1988 | F.A. Cup | 3rd Round | Sat 09 Jan | Hartlepool U. | 1 - 2 | Luton Town |
| League Cup | 1st Round | Wed 26 Aug | Hartlepool U. | 0 - 1 | Scunthorpe U. |
| Scunthorpe United won 4-1 on aggregate |
| (Associate Members) | Northern Section Semi-Final | Wed 09 Mar | Hartlepool U. | 0 - 2 | Preston N.E. |
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| 1986/1987 | F.A. Cup | 1st Round | Sat 15 Nov | Wrexham | 2 - 1 | Hartlepool U. |
| League Cup | 1st Round | Tue 02 Sep | Middlesbrough | 2 - 0 | Hartlepool U. |
| Middlesbrough won 3-1 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Two | Sat 06 Dec | Hartlepool U. | 0 - 0 | Lincoln City |
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| 1985/1986 | F.A. Cup | 2nd Round | Sat 07 Dec | Hartlepool U. | 0 - 1 | Frickley Ath. |
| League Cup | 1st Round | Wed 04 Sep | Hartlepool U. | 2 - 0 | Derby County |
| Derby County won 3-2 on aggregate |
| (Associate Members) | Northern Section Preliminary Round Group Seven | Tue 28 Jan | Hartlepool U. | 3 - 2 | York City |
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| 1984/1985 | F.A. Cup | 2nd Round | Sat 08 Dec | Hartlepool U. | 0 - 2 | York City |
| League Cup | 1st Round | Wed 05 Sep | Hartlepool U. | 0 - 1 | Derby County |
| Derby County won 6-1 on aggregate |
| (Associate Members) | Northern Section 1st Round | Wed 06 Feb | Lincoln City | 4 - 0 | Hartlepool U. |
| Lincoln City won 5-2 on aggregate |
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| 1983/1984 | F.A. Cup | 1st Round Replay | Wed 23 Nov | Hartlepool U. | 0 - 1 | Rotherham U. |
| after extra time, 90 minutes 0-0 |
| League Cup | 1st Round | Wed 14 Sep | Hartlepool U. | 0 - 1 | Rotherham U. |
| Rotherham United won 1-0 on aggregate |
| (Associate Members) | Northern Section 1st Round | Wed 22 Feb | Bradford City | 3 - 2 | Hartlepool U. |
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| 1982/1983 | F.A. Cup | 2nd Round Replay | Tue 14 Dec | York City | 4 - 0 | Hartlepool U. |
| League Cup | 2nd Round | Mon 25 Oct | Hartlepool U. | 4 - 2 | Derby County |
| aggregate 4-4, Derby County won on away goals rule |
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| 1981/1982 | F.A. Cup | 2nd Round | Mon 04 Jan | Hull City | 2 - 0 | Hartlepool U. |
| League Cup | 1st Round | Wed 16 Sep | Hartlepool U. | 2 - 1 | Northampton |
| Northampton Town won 3-2 on aggregate |
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| 1980/1981 | F.A. Cup | 1st Round | Sat 22 Nov | Scunthorpe U. | 3 - 1 | Hartlepool U. |
| League Cup | 1st Round | Tue 12 Aug | Hartlepool U. | 0 - 0 | York City |
| York City won 2-1 on aggregate |
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| 1979/1980 | F.A. Cup | 1st Round | Sat 24 Nov | Barnsley | 5 - 2 | Hartlepool U. |
| League Cup | 1st Round | Tue 14 Aug | Hartlepool U. | 2 - 1 | Chesterfield |
| Chesterfield won 6-3 on aggregate |
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| 1978/1979 | F.A. Cup | 3rd Round | Thu 18 Jan | Hartlepool U. | 2 - 6 | Leeds Utd. |
| League Cup | 1st Round | Tue 15 Aug | Hartlepool U. | 1 - 1 | Rotherham U. |
| Rotherham United won 6-1 on aggregate |
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| 1977/1978 | F.A. Cup | 4th Round | Sat 28 Jan | Ipswich Town | 4 - 1 | Hartlepool U. |
| League Cup | 1st Round | Tue 16 Aug | Hartlepool U. | 1 - 2 | Grimsby Town |
| Grimsby Town won 5-1 on aggregate |
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| 1976/1977 | F.A. Cup | 1st Round | Sat 20 Nov | Chester | 1 - 0 | Hartlepool* |
| League Cup | 1st Round | Wed 18 Aug | Hartlepool* | 1 - 2 | Huddersfield |
| Huddersfield Town won 4-1 on aggregate |
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| 1975/1976 | F.A. Cup | 3rd Round | Sat 03 Jan | Man. City | 6 - 0 | Hartlepool* |
| League Cup | 1st Round | Mon 25 Aug | Hartlepool* | 2 - 1 | Halifax Town |
| Halifax Town won 5-3 on aggregate |
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| 1974/1975 | F.A. Cup | 2nd Round Replay | Tue 17 Dec | Lincoln City | 0 - 1 | Hartlepool* |
| League Cup | 4th Round Replay | Mon 25 Nov | Aston Villa | 6 - 1 | Hartlepool* |
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| 1973/1974 | F.A. Cup | 1st Round | Sat 24 Nov | Altrincham | 2 - 0 | Hartlepool* |
| League Cup | 1st Round | Wed 29 Aug | Rochdale | 5 - 3 | Hartlepool* |
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| 1972/1973 | F.A. Cup | 1st Round 2nd Replay | Mon 27 Nov | Hartlepool* | 1 - 2 | Scunthorpe U. |
| after extra time, 90 minutes ?-? |
| League Cup | 2nd Round | Tue 05 Sep | Coventry City | 1 - 0 | Hartlepool* |
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| 1971/1972 | F.A. Cup | 2nd Round | Sat 11 Dec | Boston Utd. | 2 - 1 | Hartlepool* |
| League Cup | 1st Round Replay | Mon 23 Aug | Hartlepool* | 0 - 1 | Barnsley |
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| 1970/1971 | F.A. Cup | 1st Round | Sat 21 Nov | Rhyl | 1 - 0 | Hartlepool* |
| League Cup | 1st Round | Wed 19 Aug | Hartlepool* | 2 - 3 | York City |
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| 1969/1970 | F.A. Cup | 2nd Round | Sat 06 Dec | Hartlepool* | 0 - 1 | Wrexham |
| League Cup | 2nd Round | Wed 03 Sep | Hartlepool* | 1 - 3 | Derby County |
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| 1968/1969 | F.A. Cup | 1st Round Replay | Tue 19 Nov | Rotherham U. | 3 - 0 | Hartlepool* |
| League Cup | 1st Round | Wed 14 Aug | Bradford City | 3 - 2 | Hartlepool* |
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| 1967/1968 | F.A. Cup | 1st Round | Sat 09 Dec | Hartlepools* | 2 - 3 | Bury |
| League Cup | 2nd Round | Wed 13 Sep | Derby County | 4 - 0 | Hartlepools* |
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| 1966/1967 | F.A. Cup | 1st Round | Sat 26 Nov | Shrewsbury Tn. | 5 - 2 | Hartlepools* |
| League Cup | 1st Round Replay | Wed 31 Aug | Hartlepools* | 1 - 2 | Bradford P.A. |
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| 1965/1966 | F.A. Cup | 3rd Round | Mon 24 Jan | Huddersfield | 3 - 1 | Hartlepools* |
| League Cup | 2nd Round | Wed 22 Sep | Leeds Utd. | 4 - 2 | Hartlepools* |
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| 1964/1965 | F.A. Cup | 2nd Round Replay | Wed 09 Dec | Darlington | 4 - 1 | Hartlepools* |
| League Cup | 1st Round | Wed 02 Sep | Chesterfield | 3 - 0 | Hartlepools* |
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| 1963/1964 | F.A. Cup | 1st Round | Sat 16 Nov | Hartlepools* | 0 - 1 | Lincoln City |
| League Cup | 1st Round | Wed 04 Sep | Lincoln City | 3 - 2 | Hartlepools* |
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| 1962/1963 | F.A. Cup | 1st Round | Sat 03 Nov | Carlisle Utd. | 2 - 1 | Hartlepools* |
| League Cup | 1st Round Replay | Thu 13 Sep | Barnsley | 2 - 1 | Hartlepools* |
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| 1961/1962 | F.A. Cup | 3rd Round | Sat 06 Jan | Fulham | 3 - 1 | Hartlepools* |
| League Cup | 1st Round | Mon 11 Sep | Bristol Rvs. | 2 - 1 | Hartlepools* |
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| 1960/1961 | F.A. Cup | 1st Round | Sat 05 Nov | Halifax Town | 5 - 1 | Hartlepools* |
| League Cup | 1st Round | Tue 11 Oct | Oldham Ath. | 2 - 1 | Hartlepools* |
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| 1959/1960 | F.A. Cup | 1st Round | Sat 14 Nov | Bury | 5 - 0 | Hartlepools* |
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| 1958/1959 | F.A. Cup | 2nd Round | Sat 06 Dec | Barrow | 2 - 0 | Hartlepools* |
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| 1957/1958 | F.A. Cup | 2nd Round | Sat 07 Dec | Stockport Co. | 2 - 1 | Hartlepools* |
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| 1956/1957 | F.A. Cup | 3rd Round | Sat 05 Jan | Hartlepools* | 3 - 4 | Man. Utd. |
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| 1955/1956 | F.A. Cup | 3rd Round | Sat 07 Jan | Hartlepools* | 0 - 1 | Chelsea |
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| 1954/1955 | F.A. Cup | 4th Round Replay | Wed 02 Feb | Nottm. Forest | 2 - 1 | Hartlepools* |
| after extra time, 90 minutes ?-? |
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| 1953/1954 | F.A. Cup | 3rd Round | Sat 09 Jan | Stoke City | 6 - 2 | Hartlepools* |
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| 1952/1953 | F.A. Cup | 2nd Round | Sat 06 Dec | Tranmere Rvs. | 2 - 1 | Hartlepools* |
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| 1951/1952 | F.A. Cup | 3rd Round | Sat 12 Jan | Burnley | 1 - 0 | Hartlepools* |
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| 1950/1951 | F.A. Cup | 2nd Round | Sat 09 Dec | Hartlepools* | 1 - 2 | Oldham Ath. |
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| 1949/1950 | F.A. Cup | 2nd Round Replay | Thu 15 Dec | Norwich City | 5 - 1 | Hartlepools* |
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| 1948/1949 | F.A. Cup | 1st Round | Sat 27 Nov | Hartlepools* | 1 - 3 | Chester |
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| 1947/1948 | F.A. Cup | 2nd Round Replay | Sat 20 Dec | Brighton & HA | 2 - 1 | Hartlepools* |
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| 1946/1947 | F.A. Cup | 2nd Round | Sat 14 Dec | Rochdale | 6 - 1 | Hartlepools* |
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| 1945/1946 | F.A. Cup | 1st Round | Sat 24 Nov | Gateshead | 6 - 2 | Hartlepools* |
| Gateshead won 8-3 on aggregate |
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| 1938/1939 | F.A. Cup | 2nd Round | Sat 10 Dec | Hartlepools* | 0 - 2 | Q.P.R. |
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| 1937/1938 | F.A. Cup | 2nd Round | Sat 11 Dec | Tranmere Rvs. | 3 - 1 | Hartlepools* |
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| 1936/1937 | F.A. Cup | 2nd Round Replay | Wed 16 Dec | Hartlepools* | 1 - 2 | Crewe Alex. |
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| 1935/1936 | F.A. Cup | 3rd Round Replay | Tue 14 Jan | Grimsby Town | 4 - 1 | Hartlepools* |
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| 1934/1935 | F.A. Cup | 2nd Round | Sat 08 Dec | Hartlepools* | 0 - 4 | Coventry City |
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| 1933/1934 | F.A. Cup | 2nd Round Replay | Wed 13 Dec | Hartlepools* | 1 - 2 | Halifax Town |
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| 1932/1933 | F.A. Cup | 2nd Round | Sat 10 Dec | Walsall | 2 - 1 | Hartlepools* |
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| 1931/1932 | F.A. Cup | 1st Round | Sat 28 Nov | Chester | 4 - 1 | Hartlepools* |
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| 1930/1931 | F.A. Cup | 1st Round | Sat 29 Nov | Hartlepools* | 2 - 3 | Stockport Co. |
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| 1929/1930 | F.A. Cup | 1st Round | Sat 30 Nov | Scunthorpe U. | 1 - 0 | Hartlepools* |
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| 1928/1929 | F.A. Cup | 1st Round | Sat 24 Nov | Spennymoor | 5 - 2 | Hartlepools* |
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| 1927/1928 | F.A. Cup | 1st Round | Sat 26 Nov | Halifax Town | 3 - 0 | Hartlepools* |
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| 1926/1927 | F.A. Cup | 1st Round | Sat 27 Nov | Carlisle Utd. | 6 - 2 | Hartlepools* |
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| 1925/1926 | F.A. Cup | 1st Round 3rd Replay | Wed 09 Dec | Hartlepools* | 1 - 2 | Blyth |
| played at Roker Park |
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| 1924/1925 | F.A. Cup | 1st Round | Sat 10 Jan | Newcastle Utd. | 4 - 1 | Hartlepools* |
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| * Hartlepool United were formerly known as 'Hartlepool', 'Hartlepools' |
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