FA Cup 2023/24, Extra Preliminary Round |
 | 05.08.2023 | | Penrith | – | Boro Rangers | | 2:1 (0:1) |
| Penrith |
FA Cup 2020/21, Extra Preliminary Round |
| 01.09.2020 | | Penrith | – | Pickering Town | | 3:2 |
| Penrith |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Penrith | – | West Auckland Town | | 2:1 (2:1) |
| Penrith |
FA Cup 2016/17, Extra Preliminary Round |
| 06.08.2016 | | Penrith | – | Sunderland RCA | | 1:0 |
| Penrith |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Penrith | – | Padiham | | 3:1 |
| Penrith |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Shildon | – | Penrith | | 0:2 |
| Shildon |
FA Cup 2013/14, Extra Preliminary Round |
| 17.08.2013 | | Penrith | – | Newcastle Benfield | | 3:1 |
| Penrith |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Penrith | – | Billingham Synthonia | | 3:2 |
| |
FA Cup 2011/12, Extra Preliminary Round |
| 24.08.2011 | | North Shields | – | Penrith | | 0:1 * |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 15.08.2009 | | Pontefract Collieries | – | Penrith | | 1:4 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Darwen | – | Penrith | | 4:7 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Winsford United | – | Penrith Town | | 1:3 |
| |
FA Cup 2007/08, Extra Preliminary Round |
| 18.08.2007 | | Squires Gate | – | Penrith Town | | 1:3 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Skelmersdale United | – | Penrith | | 1:3 |
| |
FA Cup 2002/03, Extra Preliminary Round |
| | | Penrith | – | Brandon United | | 3:2 |
| |
FA Cup 2000/01, Extra Preliminary Round |
| | | Armthorpe Welfare | – | Penrith | | 0:1 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Penrith | – | Shotton Comrades | | 4:0 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Penrith | – | Eccleshill United | | 6:0 * |
| |
FA Cup 1997/98, Third Qualifying Round |
| | | Guiseley | – | Penrith | | 1:2 |
| |
FA Cup 1997/98, Second Qualifying Round |
| | | Penrith | – | Easington Colliery | | 6:3 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Heanor Town | – | Penrith | | 1:2 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Penrith | – | Trafford | | 3:0 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Penrith | – | Dunston Federation Brewery | | 2:1 * |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Penrith | – | Billingham Town | | 4:2 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Penrith | – | Ferryhill Athletic | | 1:0 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Penrith | – | Brandon United | | 2:1 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Penrith | – | Horden Colliery Welfare | | 7:0 |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Warrington Town | – | Penrith | | 0:2 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Penrith | – | Glossop | | 6:2 |
| |
FA Cup 1984/85, Fourth Qualifying Round |
| | | Penrith | – | Formby | | 3:2 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Penrith | – | Horden Colliery Welfare | | 3:0 |
| |
FA Cup 1981/82, First Round Proper |
| 21.11.1981 | | Penrith | – | Chester | | 1:0 |
| |
FA Cup 1981/82, Fourth Qualifying Round |
| | | Penrith | – | Northwich Victoria | | 1:0 |
| |
FA Cup 1981/82, Third Qualifying Round |
| | | Penrith | – | Droylsden | | 3:2 |
| |
FA Cup 1981/82, Second Qualifying Round |
| | | Chorley | – | Penrith | | 0:1 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Penrith | – | Rossendale United | | 2:1 |
| |
FA Cup 1980/81, Third Qualifying Round |
| | | Penrith | – | Newcastle Blue Star | | 1:0 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Penrith | – | Goole Town | | 2:0 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Penrith | – | Durham City | | 6:0 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Penrith | – | Whitley Bay | | 1:0 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Clitheroe | – | Penrith | | 0:2 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Penrith | – | Morecambe | | 3:1 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Penrith | – | Nelson | | 4:0 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Penrith | – | Evenwood Town | | 3:1 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Penrith | – | Willington | | 4:2 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Netherfield | – | Penrith | | 2:3 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Penrith | – | Morecambe | | 1:0 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Penrith | – | Moss Bay | | 12:0 |
| |
FA Cup 1948/49, Second Qualifying Round |
| | | Penrith | – | High Duty Alloys | | 3:2 * |
| |
FA Cup 1948/49, First Qualifying Round |
| | | Parton United | – | Penrith | | 1:3 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Penrith | – | Bowthorn United | | 9:2 |
| |
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