| Season |
Competition |
Round Reached |
Date |
Home |
Score |
Away |
| 2012/2013 | F.A. Cup | 1st Round | Sat 03 Nov | Chesterfield | 6 - 1 | Hartlepool U. |
| League Cup | 1st Round | Sat 11 Aug | Crewe Alex. | 5 - 0 | Hartlepool U. |
| (Associate Members) | Northern 2nd Round | Tue 09 Oct | Hartlepool U. | 0 - 0 | Bradford City |
| Bradford win 3-2 on penalties |
| 2011/2012 | F.A. Cup | 1st Round | Sat 12 Nov | Hartlepool U. | 0 - 1 | Stevenage |
| League Cup | 1st Round | Tue 09 Aug | Hartlepool U. | 1 - 1 | Sheff. Utd. |
| after extra time, 90 minutes 1-1, Sheffield United won 4-3 on penalties |
| (Associate Members) | Northern 1st Round | Tue 30 Aug | Scunthorpe U. | 2 - 0 | Hartlepool U. |
| 2010/2011 | F.A. Cup | 3rd Round | Sat 08 Jan | Watford | 4 - 1 | Hartlepool U. |
| League Cup | 2nd Round | Tue 24 Aug | Hartlepool U. | 0 - 3 | Wigan Ath. |
| (Associate Members) | Northern Quarter-Final | Wed 10 Nov | Sheff. Wed. | 4 - 1 | Hartlepool U. |
| 2009/2010 | F.A. Cup | 1st Round | Sat 07 Nov | Hartlepool U. | 0 - 1 | Kettering Tn. |
| League Cup | 2nd Round | Tue 25 Aug | Hartlepool U. | 1 - 2 | Burnley |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Northern 2nd Round | Tue 06 Oct | Hartlepool U. | 0 - 2 | Grimsby Town |
| 2008/2009 | F.A. Cup | 4th Round | Sat 24 Jan | Hartlepool U. | 0 - 2 | West Ham Utd. |
| League Cup | 3rd Round | Tue 23 Sep | Leeds Utd. | 3 - 2 | Hartlepool U. |
| (Associate Members) | Northern 1st Round | Tue 02 Sep | Hartlepool U. | 0 - 3 | Leicester City |
| 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 Quarter-Final | Tue 13 Nov | Hartlepool U. | 1 - 1 | Morecambe |
| after extra time, 90 minutes 1-1, Morecambe won 4-2 on penalties |
| 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 2nd Round | Tue 31 Oct | Hartlepool U. | 1 - 3 | Doncaster Rvs. |
| 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 1st Round | Tue 18 Oct | Scunthorpe U. | 1 - 0 | Hartlepool U. |
| 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 Quarter-Final | Tue 30 Nov | Oldham Ath. | 3 - 1 | Hartlepool U. |
| 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 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 |
| 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 1st Round | Tue 22 Oct | Tranmere Rvs. | 5 - 0 | Hartlepool U. |
| 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 1st Round | Tue 16 Oct | Hartlepool U. | 0 - 1 | Bury |
| after extra time, 90 minutes 0-0, Bury won on the golden goal rule |
| 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 Quarter-Final | Tue 30 Jan | Lincoln City | 1 - 0 | Hartlepool U. |
| 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 Quarter-Final | Tue 22 Feb | Hartlepool U. | 1 - 2 | Carlisle Utd. |
| 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 Quarter-Final | Tue 26 Jan | Hartlepool U. | 0 - 3 | Lincoln City |
| 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 2nd Round | Tue 06 Jan | Hartlepool U. | 1 - 2 | Scunthorpe U. |
| 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 1st Round | Tue 10 Dec | Hartlepool U. | 0 - 2 | Burnley |
| 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 Preliminary Round Group One | Tue 07 Nov | Hartlepool U. | 3 - 2 | Blackpool |
| 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 Preliminary Round Group One | Tue 08 Nov | Hartlepool U. | 0 - 2 | Darlington |
| 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 Preliminary Round Group Four | Tue 09 Nov | York City | 2 - 0 | Hartlepool U. |
| 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 1st Round | Tue 12 Jan | Stockport Co. | 1 - 0 | Hartlepool U. |
| 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 Quarter-Final | Tue 04 Feb | Stockport Co. | 3 - 0 | Hartlepool U. |
| 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 1st Round | Tue 22 Jan | Bradford City | 3 - 2 | Hartlepool U. |
| 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 Preliminary Round Group Six | Tue 28 Nov | Hartlepool U. | 1 - 4 | Rotherham U. |
| 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 Preliminary Round Group Four | Tue 13 Dec | Hartlepool U. | 0 - 2 | York City |
| 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 Semi-Final | Wed 09 Mar | Hartlepool U. | 0 - 2 | Preston N.E. |
| 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 Preliminary Round Group Two | Sat 06 Dec | Hartlepool U. | 0 - 0 | Lincoln City |