FA Cup 2023/24, Extra Preliminary Round |
 | 05.08.2023 | | Horndean | – | Portland United | | 3:0 (0:0) |
| Horndean |
FA Cup 2022/23, Extra Preliminary Round |
| 06.08.2022 | | Lymington Town | – | Portland United | | 2:0 (0:0) |
| Lymington |
FA Cup 2021/22, Extra Preliminary Round |
| 10.08.2021 | | Bournemouth | – | Portland United | | 3:1 (1:0) * |
| Bournemouth |
FA Cup 2021/22, Extra Preliminary Round |
| 07.08.2021 | | Portland United | – | Bournemouth | | 2:2 (0:1) |
| Isle of Portland |
FA Cup 2020/21, Extra Preliminary Round |
| 01.09.2020 | | Portland United | – | Clevedon Town | | 0:1 |
| Isle of Portland |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Portland United | – | Salisbury | | 0:1 (0:1) |
| Isle of Portland |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Longlevens | – | Portland United | | 0:2 (0:1) |
| Longlevens |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Portland United | – | Hamworthy United | | 4:3 (2:1) |
| Isle of Portland |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Team Solent | – | Portland United | | 0:3 (0:3) |
| Southampton Test Park Sports Ground |
FA Cup 2018/19, Preliminary Round |
| 25.08.2018 | | Portland United | – | Bitton | | 0:2 |
| Isle of Portland |
FA Cup 2018/19, Extra Preliminary Round |
| 11.08.2018 | | Clevedon Town | – | Portland United | | 1:2 (0:1) |
| Clevedon |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Portland United | – | Paulton Rovers | | 0:3 (0:1) |
| Isle of Portland |
FA Cup 2017/18, Extra Preliminary Round |
| 05.08.2017 | | Plymouth Parkway | – | Portland United | | 0:1 |
| Plymouth |
FA Cup 2005/06, Extra Preliminary Round |
| 20.08.2005 | | Odd Down | – | Portland United | | 2:0 |
| |
FA Cup 2004/05, Extra Preliminary Round |
| | | Portland United | – | Bridgwater Town | | 0:3 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Highworth Town | – | Portland United | | 4:3 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Corsham Town | – | Portland United | | 3:1 |
| |
FA Cup 2002/03, Extra Preliminary Round |
| | | Portland United | – | Welton Rovers | | 6:2 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Salisbury | – | Portland United | | 3:0 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Frome Town | – | Portland United | | 2:0 * |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Portland United | – | Frome Town | | 1:1 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Trowbridge Town | – | Portland United | | 3:0 |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Taunton | – | Portland United | | 2:0 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Portland United | – | Bridport | | 3:1 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Portland United | – | Poole Town | | 0:2 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Portland United | – | Glastonbury | | 4:2 * |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Glastonbury | – | Portland United | | 2:2 |
| |
FA Cup 1965/66, Fourth Qualifying Round |
| | | Yeovil Town | – | Portland United | | 1:0 * |
| |
FA Cup 1965/66, Fourth Qualifying Round |
| | | Portland United | – | Yeovil Town | | 1:1 |
| |
FA Cup 1965/66, Third Qualifying Round |
| | | Salisbury | – | Portland United | | 0:3 |
| |
FA Cup 1965/66, Second Qualifying Round |
| | | Poole Town | – | Portland United | | 0:2 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Portland United | – | Dorchester Town | | 4:1 |
| |
FA Cup 1964/65, Third Qualifying Round |
| | | Salisbury | – | Portland United | | 5:1 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Warminster Town | – | Portland United | | 1:3 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Portland United | – | Bridport | | 2:4 |
| |
FA Cup 1962/63, Second Qualifying Round |
| | | Portland United | – | Dorchester Town | | 1:3 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Bridport | – | Portland United | | 1:5 |
| |
FA Cup 1961/62, Third Qualifying Round |
| | | Portland United | – | Dorchester Town | | 0:3 |
| |
FA Cup 1961/62, Second Qualifying Round |
| | | Portland United | – | Bridport | | 4:3 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Warminster Town | – | Portland United | | 3:1 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Portland United | – | Salisbury | | 2:3 |
| |
FA Cup 1958/59, Fourth Qualifying Round |
| | | Newport IOW | – | Portland United | | 3:1 * |
| |
FA Cup 1958/59, Fourth Qualifying Round |
| | | Portland United | – | Newport IOW | | 2:2 |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Portland United | – | Poole Town | | 1:0 |
| |
FA Cup 1958/59, Second Qualifying Round |
| | | Portland United | – | Warminster Town | | 3:0 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Portland United | – | Ilminster Town | | 7:0 |
| |
FA Cup 1957/58, Fourth Qualifying Round |
| | | Newport IOW | – | Portland United | | 5:0 |
| |
FA Cup 1957/58, Third Qualifying Round |
| | | Portland United | – | Bridport | | 2:1 |
| |
FA Cup 1957/58, Second Qualifying Round |
| | | Portland United | – | Poole Town | | 3:1 |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Poole Town | – | Portland United | | 2:0 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Portland United | – | Ilminster Town | | 9:0 |
| |
FA Cup 1955/56, Third Qualifying Round |
| | | Portland United | – | Poole Town | | 1:4 |
| |
FA Cup 1955/56, Second Qualifying Round |
| | | Portland United | – | Ilminster Town | | 5:0 |
| |
FA Cup 1954/55, Third Qualifying Round |
| | | Portland United | – | Dorchester Town | | 1:5 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Portland United | – | Bridport | | 4:2 |
| |
FA Cup 1953/54, Fourth Qualifying Round |
| | | Llanelli | – | Portland United | | 6:5 |
| |
FA Cup 1953/54, Third Qualifying Round |
| | | Portland United | – | Bournemouth Gasworks Athletic | | 4:1 |
| |
FA Cup 1953/54, Second Qualifying Round |
| | | Dorchester Town | – | Portland United | | 1:3 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Portland United | – | Shaftesbury | | 11:1 |
| |
FA Cup 1952/53, Second Qualifying Round |
| | | Bournemouth Gasworks Athletic | – | Portland United | | 5:1 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Portland United | – | Shaftesbury | | 3:1 |
| |
FA Cup 1951/52, Third Qualifying Round |
| | | Portland United | – | Lymington | | 1:2 * |
| |
FA Cup 1951/52, Third Qualifying Round |
| | | Lymington | – | Portland United | | 1:1 |
| |
FA Cup 1951/52, Second Qualifying Round |
| | | Bournemouth Gasworks Athletic | – | Portland United | | 1:3 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Dorchester Town | – | Portland United | | 2:3 * |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Portland United | – | Dorchester Town | | 1:1 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Dorchester Town | – | Portland United | | 6:3 |
| |
FA Cup 1949/50, First Qualifying Round |
| | | Bournemouth Amateurs | – | Portland United | | 3:1 |
| |
FA Cup 1949/50, Preliminary Round |
| | | Longfleet St Mary's | – | Portland United | | 0:1 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Hamworthy | – | Portland United | | 0:1 |
| |
FA Cup 1948/49, Extra Preliminary Round |
| | | Portland United | – | Longfleet St Mary's | | 2:4 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Bournemouth Gasworks Athletic | – | Portland United | | 4:0 |
| |
FA Cup 1947/48, Extra Preliminary Round |
| | | Lymington | – | Portland United | | 1:2 |
| |
USSR
Ukraine
Azerbaijan
Armenia
Belarus
Kazakhstan
Moldova
Uzbekistan
Austria
England
Belgium
Bulgaria
Hungary
Germany
Netherlands
Georgia
Iceland
Spain
Italy
Latvia
Lithuania
Norway
Poland
Portugal
Serbia
Slovenia
France
Croatia
Montenegro
Czech
Sweden
Scotland
Estonia
Argentina
USA
Canada
China
Australia
