| Haringey Borough | | 2000 | | Extra Preliminary Round | 10-09-2000 | | Haringey Borough | London Ladies | 5-3 | | Preliminary Round | 24-09-2000 | | Haringey Borough | Billericay Town | 4-1 | | First Round | 05-11-2000 | | Haringey Borough | Tottenham Hotspur | 1-7 | | 2001 | | 2nd Qualifying Round | 30-09-2001 | | Colney Heath | Haringey Borough | 1-0 | | 2002 | | 1st Qualifying Round | 08-09-2002 | | Haringey Borough | Woking | 1-2 | | 2003 | | 1st Qualifying Round | 07-09-2003 | | Haringey Borough | Basildon United | 5-1 | | 2nd Qualifying Round | 28-09-2003 | | Haringey Borough | Tottenham Hotspur | 0-7 | | 2004 | | 1st Qualifying Round | 05-09-2004 | | Haringey Borough | Chelmsford City | 1-7 | | 2005 | | 1st Qualifying Round | 11-09-2005 | | Haringey Borough | Kent Magpies | 7-3 | | 2nd Qualifying Round | 25-09-2005 | | Haringey Borough | Banbury United | 10-1 | | First Round | 23-10-2005 | | Haringey Borough | Staines Town | 2-5 | | 2006 | | Preliminary Round | 10-09-2006 | | Haringey Borough | Tower Hamlets | 5-6 | |
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| 2007 | | 1st Qualifying Round | 16-09-2007 | | Wingate & Finchley | Haringey Borough | 3-3 | |
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| 2008 | | 1st Qualifying Round | 28-09-2008 | | Uxbridge United | Haringey Borough | 0-15 | | 2nd Qualifying Round | 12-10-2008 | | Old Actonians | Haringey Borough | 1-4 | | 3rd Qualifying Round | 09-11-2008 | | Haringey Borough | AFC Wimbledon | 2-3 | |
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| 2009 | | 1st Qualifying Round | 27-09-2009 | | Haringey Borough | Wandgas | 4-1 | | 2nd Qualifying Round | 11-10-2009 | | Panthers | Haringey Borough | 3-4 | | 3rd Qualifying Round | 25-10-2009 | | Haringey Borough | Eastbourne Town | 2-1 | | First Round | 08-11-2009 | | Haringey Borough | Barking | 3-1 | | Second Round | 29-11-2009 | | Lewes | Haringey Borough | 5-1 | | 2010 | | 1st Qualifying Round | 10-10-2010 | | Wandgas | Haringey Borough | 3-3 | | 2nd Qualifying Round | 24-10-2010 | | Mauritius Sports Association (MSA) | Haringey Borough | 2-0 | |
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| 2011 | | 1st Qualifying Round | 02-10-2011 | | Leyton | Haringey Borough | 3-1 | | 2012 | | 1st Qualifying Round | 30-09-2012 | | Kick In Kulan I Krysset United (KIKK) | Haringey Borough | 3-1 | | 2013 | | 1st Qualifying Round | 22-09-2013 | | Kick In Kulan I Krysset United (KIKK) | Haringey Borough | 7-0 | | 2014 | | 1st Qualifying Round | 28-09-2014 | | Haringey Borough | Long Lane | 2-4 | | 2015 | | 1st Qualifying Round | 06-09-2015 | | Haringey Borough | Leverstock Green | 6-0 | | 2nd Qualifying Round | 20-09-2015 | | Royston Town | Haringey Borough | 0-2 | | 3rd Qualifying Round | 11-10-2015 | | Enfield Town | Haringey Borough | 4-0 | | 2016 | | 2nd Qualifying Round | 18-09-2016 | | Haringey Borough | Chelmsford City | 12-0 | | 3rd Qualifying Round | 09-10-2016 | | Haringey Borough | Chichester City | 2-8 | | 2017 | | 3rd Qualifying Round | 08-10-2017 | | Godalming Town | Haringey Borough | 5-0 | | 2019 | | Preliminary Round | 01-09-2019 | | Phoenix Sports | Haringey Borough | 5-1 | | 2020 | | Preliminary Round | 20-09-2020 | | Haringey Borough | Fulham | 1-2 | | 2021 | | 2nd Qualifying Round | 03-10-2021 | | Haringey Borough | Clapton Community | 3-6 | | 2022 | | 2nd Qualifying Round | 02-10-2022 | | Hastings United | Haringey Borough | 2-1 | | 2023 | | 2nd Qualifying Round | 01-10-2023 | | Haringey Borough | Bexhill United | 8-0 | | 3rd Qualifying Round | 22-10-2023 | | Haringey Borough | Langford | 5-0 | | First Round | 12-11-2023 | | Hertford Town | Haringey Borough | 1-3 | | Second Round | 26-11-2023 | | Haringey Borough | Moneyfields | 1-3 | | 2024 | | 2nd Qualifying Round | 22-09-2024 | | Haringey Borough | Royston Town | 1-3 |
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