| DATE | HOME | SCORE/KO | W/L/D | AWAY | VENUE | COMPETITION |
|---|---|---|---|---|---|---|
| Jul 26 | ||||||
| Sat 04 | Wimborne Town | 2-0 |  | Portland United | Wyatt Homes Stadium? | Pre-Season Friendly |
| Sat 11 | Saltash United | 1-1 |  | Portland United + Reserves | Waterways Stadium | Pre-Season Friendly |
| Tue 14 | Portland United | 7-0 |  | Christchurch | Camp & Satherley Stadium | Pre-Season Friendly |
| Sat 18 | Sherborne Town | 2-0 | | Portland United | Raleigh Grove | Pre-Season Friendly |
| Tue 21 | Portland United | 7:45pm | Bashley | Camp & Satherley Stadium | Pre-Season Friendly | |
| Sat 25 | Bridport | 3:00pm | Portland United | St Mary's Field | Pre-Season Friendly | |
| Aug 26 | ||||||
| Sat 01 | Portland United | 12:00pm | Poole Town Under 23s | CANCELLED | Pre-Season Friendly | |
| Sat 08 | Portland United | 3:00pm | Sturminster Newton United | Camp & Satherley Stadium | FA Cup EP Round | |
| Tue 11 | Portland United | 7:45pm | Westbury United | Camp & Satherley Stadium | Southern League | |
| Sat 15 | Bristol Manor Farm | 3:00pm | Portland United | The Creek Community Stadium | Southern League | |
| Sat 29 | Portland United | 3:00pm | Hungerford Town | Camp & Satherley Stadium | FA Trophy (1Q) | |
| Mon 31 | Portland United | 3:00pm | Shaftesbury | Camp & Satherley Stadium | Southern League | |
| Sep 26 | ||||||
| Sat 05 | Slimbridge AFC | 3:00pm | Portland United | Thornhill Park | Southern League | |
| Wed 16 | Paulton Rovers | 7:45pm | Portland United | Winterfield Stadium | Southern League | |
| Sat 19 | Portland United | 3:00pm | Larkhall Athletic | Camp & Satherley Stadium | Southern League | |
| Sat 26 | Willand Rovers | 3:00pm | Portland United | Stan Robinson Stadium | Southern League | |
| Tue 29 | Portland United | 7:45pm | Falmouth Town | Camp & Satherley Stadium | Southern League | |
| Oct 26 | ||||||
| Sat 03 | Bidefird AFC | 3:00pm | Portland United | The Sports Ground | Southern League | |
| Sat 10 | Portland United | 3:00pm | Sporting Club Inkberrow | Camp & Satherley Stadium | Southern League | |
| Tue 13 | Portland United | 7:45pm | Exmouth Town | Camp & Satherley Stadium | Southern League | |
| Sat 17 | Tiverton Town | 3:00pm | Portland United | Slee Blackwell Solicitors Stadium | Southern League | |
| Tue 20 | Melksham Town | 7:45pm | Portland United | Meads of Melksham Community Stadium | Southern League | |
| Sat 24 | Portland United | 3:00pm | Bishops Cleave | Camp & Satherley Stadium | Southern League | |
| Tue 27 | Portland United | 7:45pm | Paulton Rovers | Camp & Satherley Stadium | Southern League | |
| Sat 31 | Dorchester Town | 3:00pm | Portland United | The Avenue Stadium | Southern League | |
| Nov 26 | ||||||
| Sat 07 | Portland United | 3:00pm | Hartpury | Camp & Satherley Stadium | Southern League | |
| Tue 10 | Falmouth Town | 7:45pm | Portland United | Bickland Park | Southern League | |
| Sat 14 | Swindon Supermarine | 3:00pm | Portland United | The Imagine Cruising Stadium | Southern League | |
| Sat 21 | Portland United | 3:00pm | Barnstaple Town | Camp & Satherley Stadium | Southern League | |
| Sat 28 | Larkhall Athletic | 3:00pm | Portland United | Plain Ham | Southern League | |
| Dec 26 | ||||||
| Sat 05 | Portland United | 3:00pm | Willand Rovers | Camp & Satherley Stadium | Southern League | |
| Sat 12 | Portland United | 3:00pm | Worcester Raiders | Camp & Satherley Stadium | Southern League | |
| Sat 19 | Hungerford Town | 3:00pm | Portland United | Town Ground | Southern League | |
| Sat 26 | Portland United | 3:00pm | Weymouth | Camp & Satherley Stadium | Southern League | |
| Jan 27 | ||||||
| Sat 02 | Shaftesbury | 3:00pm | Portland United | Cockrams | Southern League | |
| Sat 09 | Sporting Club Inkberrow | 3:00pm | Portland United | Sands Road | Southern League | |
| Sat 16 | Portland United | 3:00pm | Bideford AFC | Camp & Satherley Stadium | Southern League | |
| Sat 23 | Exmouth Town | 3:00pm | Portland United | Complete Infrastructure Satadium | Southern League | |
| Sat 30 | Portland United | 3:00pm | Tiverton Town | Camp & Satherley Stadium | Southern League | |
| Feb 27 | ||||||
| Sat 06 | Bishops Cleave | 3:00pm | Portland United | Everyone's Energy Stadium | Southern League | |
| Sat 13 | Portland United | 3:00pm | Melksham Town | Camp & Satherley Stadium | Southern League | |
| Sat 20 | Portland United | 3:00pm | Dorchester Town | Camp & Satherley Stadium | Southern League | |
| Sat 27 | Hartpury | 3:00pm | Portland United | 4ED Hartpury Stadium | Southern League | |
| Mar 27 | ||||||
| Sat 06 | Westbury United | 3:00pm | Portland United | Meadow Lane | Southern League | |
| Sat 13 | Portland United | 3:00pm | Slimbridge | Camp & Satherley Stadium | Southern League | |
| Sat 20 | Worcester Raiders | 3:00pm | Portland United | DOADC Stadium | Southern League | |
| Fri 26 | Portland United | 3:00pm | Bristol Manor Farm | Camp & Satherley Stadium | Southern League | |
| Mon 29 | Weymouth | 3:00pm | Portland United | The Bob Lucas Stadium | Southern League | |
| Apr 27 | ||||||
| Sat 03 | Portland United | 3:00pm | Hungerford Town | Camp & Satherley Stadium | Southern League | |
| Sat 10 | Barnstaple Town | 3:00pm | Portland United | Mill Road | Southern League | |
| Sat 17 | Portland United | 3:00pm | Swindon Supermarine | Camp & Satherley Stadium | Southern League | |
Please be reminded that the above fixtures are subject to change
