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 |
| |
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