Club Main sponsor
| Date | Result | Scorers |
| 18/01/2020 | Highworth Town 1-3 Winchester City | Bailey, Barron (pen), Balmer |
| 11/01/2020 | Winchester City 2-0 Bristol Manor Farm | Mlambo. Bailey |
| 07/01/2020 | Winchester City 4-0 Sholing | Bailey(2), Panesar-Dower, Preston |
| 04/01/2020 | AFC Totton 0-0 Winchester City | |
| 01/01/2020 | Winchester City 5-1 Basingstoke Town | L King, Balmer, Douglas(2), Griggs |
| 26/12/2019 | Thatcham Town 2-1 Winchester City | Carr |
| 14/12/2019 | Winchester City 3-0 Willand Rovers | Barron(3) |
| 07/12/2019 | Frome Town 2-0 Winchester City | |
| 03/12/2019 | Winchester City 0-1 Moneyfields | |
| 30/11/2019 | Winchester City 1-1 Paulton Rovers | Barron |
| 23/11/2019 | Cirencester 3-4 Winchester City | Hayward, Carr, Griggs, Balmer |
| 19/11/2019 | Winchester City 4-0 Thatcham Town | Hill, Panasar-Dower, Griggs, Balmer |
| 16/11/2019 | Winchester City 3-2 Slimbridge | Barron, Carr, Hill |
| 12/11/2019 | Winchester City 6-0 Infinity | Mlambo(3), Balmer(2), Carr |
| 09/11/2019 | Moneyfields 0-2 Winchester City | Mlambo, L King |
| 22/09/2019 | Thame United 5-3 Winchester City | Barron(2), Carr |
| 19/09/2019 | Barnstaple Town 1-6 Winchester City | Mlambo(3), Hill, Barron, Carr |
| 15/09/2019 | Winchester City 3-3 Thame United | Balmer, Barron, Hill |
| 08/10/2019 | Winchester City 2-0 Farnborough | Hill, Francis |
| 05/10/2019 | Sholing 1-2 Winchester City | Barron, Panesar-Dower |
| 28/09/2019 | Winchester City 0-3 Cinderford Town | |
| 24/09/2019 | Mangotsfield United 1-2 Winchester City |
Balmer, Williamson |
| 17/09/2019 | Hythe and Dibden 3-8 Winchester City |
Mlambo(2), Barron, Balmer, D King, Smith, Bailey, Hill |
| 14/09/2019 | Evesham United 2-0 Winchester City | |
| 07/09/2019 | Winchester City 0-3 Taunton Town | |
| 03/09/2019 | AFC Stoneham 1-3 Winchester City | Bailey, Barron, griggs |
| 31/08/2019 | Winchester City 3-0 Melksham Town | Bailey (2), Balmer |
| 26/08/2019 | Basingstoke Town 1-1 Winchester City | Barron |
| 23/04/2019 | Winchester City 1-1 AFC Stoneham | Barron |
| 20/08/2019 | Winchester City 2-1 AFC Totton | Mlambo (2) |
| 17/08/2019 | Bristol manor farm 3-3 Winchester City | Mlambo (2), Carr |
| Date | Result | Scorers |
| 27/04/2019 | Cinderford Town 0-0 Winchester City | |
| 22/04/2019 | Winchester City 3-0 Blackfield and Langley | Bailey(2) Barron |
| 20/04/2019 | Melksham Town 1-4 Winchester City | og, Bailey(2), Mlambo |
| 13/04/2019 | Winchester City 1-3 Bristol Manor Farm | Bailey |
| 09/04/2019 | Winchester City 2-1 AFC Totton | Flooks, Barron |
| 06/04/2019 | Yate Town 3-2 Winchester City | Mlambo, Barron |
| 30/02/2019 | Winchester City 3-0 Fleet Town | Mitford, Cook. Barron |
| 23/03/2019 | Larkhall 0-1 Winchester City | Barron |
| 16/03/2019 | Winchester City 6-1 Slimbridge | Bailey(2), Harfield, Hill, Barron , Mlamb0 |
| 09/03/2019 | Winchester City 5-0 Street | |
| 02/03/2019 | Bideford 1-0 Winchester City | Bailey(3), Hill, Barron |
| 27/02/2019 | Highworth Town 1-4 Winchester City | Harfield(2), Cook, Bailey |
| 23/02/2019 | Winchester City 7-0 Barnstaple Town | Barron, Mlambo, Bailey, Mitford(2), Gilbert , King |
| 16/02/2019 | Evesham Town 0-2 Winchester City | Barron, Mitford |
| 26/01/2019 | Winchester City 3-2 Cirencester Town | Mlambo, OG, Mitford |
| 19/01/2019 | Paulton Rovers 0-1 Winchester City | Mlambo |
| 12/01/2019 | Thatcham Town 1-1 Winchester City | Barron |
| 05/01/2019 | Winchester City 2-2 Cinderford Town | Harfield(2) |
| 01/01/2019 | Blackfield and Langley 0-4 Winchester City | Mitford(2), Flooks, Cunningham |
| 29/12/2018 | Winchester City 4-0 Mangotsfield United | Mitford(3), Gilbert |
| 26/12/2018 | Winchester City 0-3 Moneyfields | |
| 22/12/2018 | Bristol Manor Farm 3-1 Winchester City | Bailey |
| 15/12/2018 | Winchester City 2-2 Bideford | Mitford, Harfield |
| 08/12/2018 | Street 0-2 Winchester City | Mitford, Cunningham |
| 01/12/2018 | Winchester City 1-0 Larkhall Athletic | Hill |
| 27/11/2018 | Fleet Town 1-2 Winchester City | Rawkins, Mitford |
| 24/11/2018 | Slimbridge 1-3 Winchester City | Griggs, Barron, Bailey |
| 17/11/2018 | Winchester City 0-1- Yate Town | |
| 13/11/2018 | Winchester City 1-2 Evesham Town | Carr |
| 03/11/2018 | Barnstaple Town 3-2 Winchester City | Bailey, mitford |
| 27/10/2018 | Winchester City 1-1 Highworth Town | Bailey |
| 23/10/2018 | AFC Totton 1-1 Winchester City | Bailey |
| 20/10/2018 | Torquay United 4-1 Winchester City | Haywood |
| 16/10/2018 | Cirencester Town 3-2 Winchester City | Bailey, Barron |
| 10/10/2018 | Winchester City 0-0 Hartley Witney (HW AET) | |
| 06/10/2018 |
Winchester City 3-0 Cirencester Town |
Carr, Mlambo, Harward(pen) |
| 02/10/2018 |
Winchestre City 3-3 Slimbridge (AET) (5-6 on penalties) |
Barron, Mitford (2) |
| 29/09/2018 |
Slimbridge 2-2 Winchester City |
Mitford, Barron |
| 22/09/2018 |
Merhyr Town 1-4 Winchester City |
Mitford(3), Barron |
| 15/09/2018 |
Winchester City 2-3 Paulton Rovers |
Mitford, Rusher |
| 12/09/2018 |
Winchester City 2-1 Frome Town (AET) |
Mitford, Cocklin |
| 08/09/2018 |
Frome Town 1-1 Winchester City |
Mitford |
| 04/09/2018 |
Winchester City 1-1 Gosport Town (Gos win on pens) |
Roberts |
| 01/09/2018 |
Winchester City 2-2 Melksham Town |
Cook, Mlambo |
| 27/08/2018 |
Moneyfields 0-2 Winchester City |
Barron, Bailey |
| 25/08/2018 |
Winchester City 1-0 Bournemouth Poppies |
Mitford |
| 21/08/2018 |
Thatcham Town |
Rusher, Cook, Mitford |
| 18/08/2018 |
Mangotsfield United 1-2 Winchester City |
Bailey, Mitford |
| Date | Result | Scorers |
| 28/04/2018 |
Bideford 2-0 Winchester City |
|
| 24/04/2018 |
Winchester City 1-2 Cirencester |
Mlambo |
| 21/04/2018 |
Winchester City 2-0 North Leigh |
Carr, Bailey |
| 18/04/2018 |
Winchester City 0-5 Winchester City |
|
| 14/04/2018 |
Swndown Supermarine 1-1 Winchester City |
Carr |
| 12/04/2018 |
AFC Totton 1-0 Winchester City |
|
| 10/04/2018 |
Salisbury 2-2 Winchester City |
Tomasso, Harfield |
| 07/04/2018 |
Winchester City 4-1 Yate Town |
Bailey, Barron, Tomasso, Mlambo |
| 24/03/2018 |
Evesham 1-0 Winchester Ccty |
|
| 17/03/2018 |
Winchester City 3-0 Slimbridge |
Davis, og, Cox |
| 06/03/2018 |
Winchester City 0-1 Blackfield & Langley |
|
| 27/02/2018 |
Winchester City 1-1 Barnstaple Town |
Cox |
| 20/02/2018 |
Bishops Cleeve 4-2 Winchester City |
Barron, Bailey |
| 17/02/2018 |
Bristol Manor Farm 4-1 Winchester City |
Williamson |
| 10/02/2018 |
Winchester City 2-0 Didcot Town |
Barron (2) |
| 03/02/2018 |
Mangotsfield United 1-1 Winxhester City |
Barron |
| 31/01/2018 |
Kidlington 1-1 Winchester City |
Cpx |
| 27/01/2018 |
Winchester City 2-0 Cinderford |
Cox, Gilbert |
| 23/01/2018 |
Winchester City 4-3 Alresford |
Bailey, Carr, Cox(2) |
| 17/01/2018 |
Slimbridge 2-0 Winchester City |
|
| 13/01/2018 |
Winchester City 3-1 Larkhall Athletic |
Barron(2), Bailey |
| 06/02/3028 |
Paulton Rovers 2-2 Winchester City |
Cox, Barron |
| 01/01/2018 |
Winchester City 1-1 AFC Totton |
Bailey |
| 26/12/2017 |
Wimborne Town 3-0 Winchester City |
|
| 23/12/2017 |
Winchester City 5-1 Shortwoood Town |
Cox(3) Bailey, Barron |
| 05/12/2017 |
Winchester City 3 - 3 Basingstoke Town (5-4 Pens) |
Gilbert, Flookes, Cook |
| 02/12/2017 | Winchester City 2-0 Evesham | Carr, Hill |
| 28/11/2017 | North Leigh 1-2 Winchester City | Bailey, Jenkinson |
| 25/11/2017 | Winchester City 2-3 Bideford | og, Bailey |
| 21/11/2017 | Winchester City 3-2 Swindon Supermarine | Bailey, Barron(2) |
| 18/11/2017 | Yate Town 1-1 Winchester City | Cox |
| 11/11/2017 | Winchester City 2-1 Bishops Cleeve | Bailey(2) |
| 04/11/2017 | Cinderford Town 2-2 Winchester City | Gilbert, Cox |
| 27/10/2017 | Winchester City 4-5 Salisbury | Cook, Bailey(2), Barron, |
| 21/10/2017 | Taunton Town 4-1 Winchester City | Bailey |
| 17/10/2017 | Winchester City 1-1- Paulton Rovers | Carr |
| 14/10/2017 | Winchester City 1-2 Bristol Manor Farm | Bailey |
| 07/10/2017 | Kidlington 3-1 Winchester City | Harfield |
| 03/10/2017 | Winchester City 1-4 AFC Totton | Andrady |
| 30/09/2017 | Barnstaple Town 1-4 Winchester City | Bailey 2, Mlambo, Flooks |
| 26/09/2017 | Didcot Town 2-3 Winchester City | Bailey 2, Carr. Mlambo |
| 23/09/2017 | Winchester City 3-0 Mangotsfield United | Cox, Carr, Bailey |
| 19/09/2017 | Winchester City 6-2 East Cowes Vics | Cox 4, og, Bailey |
| 09/09/2017 | Cirencester Town 1-0 Winchester City | |
| 02/09/2017 | Paulton Rovers 1-0 Winchester City | |
| 28/08/2017 | Winchester City 1-0 Wimborne Town | Harfield |
| 26/08/2017 | Larkhall Athletic 1-2 Winchester City | Carr, Cox |
| 19/08/2017 | Bracknell Town 0-4 Winchester City (FA Cup prelim) | Jenkinson., Carr, Flooks, Cox |
| 15/08/2017 | Winchester City 0-1 Kidlington | |
| 12/08/2017 | Shortwood 2-4 Winchester City | Bailey, Cox(3) |
2017-2018 Season preseason friendlies
5th (A) ROMSEY TOWN FC 2-2 WINCHESTER CITY
7th (H) WINCHESTER CITY 3-2 GOSPORT BOROUGH FC
11th (H) WINCHESTER CITY 0-1 HUNGERFORD TOWN FC
15th (H) WINCHESTER CITY 4-0 HANWELL TOWN FC
18th (H) SHOLING FC Abandoned
22nd (A) BASHLEY FC 0-2 WINCHESTER CITY
25th (A) BLACKFIELD & LANGLEY FC 1-1 WINCHESTER CITY
29th (H) WINCHSTER CITY 3-3 ALRESFORD TOWN
AUGUST 2017
1st (A) MONEYFIELDS FC 3-3 Winchester City
5th (H) Winchester city 0-1 FARNBOROUGH FC
| 17th Apr | Winchester City 0-1 AFC Totton | |
| 15th Apr | Tiverton Town 1-0 Winchester City | |
| 8th Apr | Winchester City 0-0 Larkhall Athletic | |
| 1st Apr | Paulton Rovers 2-0 Wincherster City | |
| 25th Mar | Winchester City 0-3 Barnstaple Town | |
| 18th Mar | Yate Town 1-0 Winchester City | |
| 14th Mar | Salisbury 3-1 Winchester City | Wilson |
| 11th Mar | Winchester City 0-1 Swindon Supermarine | |
| 7th Mar | Basingstoke Town 2-1 Winchester City | OG |
| 4th Mar | Winchester City 1-1 Taunton Town | Feeney |
| 28th Feb | Winchester City 0-0 Bideford | |
| 25th Feb | Bishops Cleeve 1-0 Winchester City | |
| 18th Feb | Winchester City 4-1 Evesham United | Green(2), Neighbour, Jenkinson, |
| 14th feb | Mangotsfield United 3-3 Winchester City | Green, Feeney, Jenkinson |
| 11th Feb | North Leigh 2-0 Winchester City | |
| 4th Feb | Winchester City 3-0 Wantage Town | Feeney(2), Green |
| 28th Jan | Bridgewater Town 0-1 Winchester City | Neighbour |
| 17th Jan | Sholing 0-1 Winchester City | Neighbour |
| 14th Jan | Larkhall Athletic 1-2 Winchester City | Neighbour, Feeney |
| 11th Jan | Evesham United 3-1 Winchester City | Feeney |
| 7th Jan | Winchester City 4-3 Shortwood United | Feeney(3) Mott |
| 2nd Jan 2017 | AFC Totton 1-3 Winchester City | Green(2), Briggs |
| 27th Dec | Winchester City 0-1 Wimborne Town | |
| 21st Dec | Winchester City 7-0 Slimbridge | Feeney(4) Tomasso, Hannam, Barron |
| 17th Dec | Bideford Town 1-2 Winchester City | Green, Feeney |
| 14th Dec | Winchester City 1-0 Yate Town | Neighbour |
| 10th Dec | Winchester City 3-2 Paulton Rovers | Feeney, Neighbour, Briggs |
| 6th Dec | Fleet Town 1-6 Winchester City | Green, Neighbour, Feeney(2). Briggs, Hill |
| 3rd Dec | Barnstaple Town 1 - 3 Winchester City | Feeney, Green, Neighbour |
| 26th Nov | Winchester City 0 - 1 Dulwich Hamlet (FA Trophy) | |
| 19th Nov | Mangotsfield United v Winchester City | Game Abandoned |
| 16th Nov | Winchester City 1 -2 North Leigh | Roberts |
| 12th Nov | Phoenix Sports 1 - 3 WCFC (FA Trophy) | Feeney (2), Jenkinson |
| 8th Nov | Salisbury 2 - 0 Winchester City (League Cup) | |
| 5th Nov | Swindon Supermarine 0 - 2 Winchester City | Feeney, Green |
| 29th Oct | Fleet Town 1 -2 Winchester City (FA Trophy) | Feeney (2) |
| 26th Oct | Winchester City 1 - 2 Bishops Cleeve | Feeney |
| 22nd Oct | Taunton Town 3 - 1 Winchester City | Neighbour |
| 18th Oct | Shortwood United 2 - 1 Winchester City | Jenkinson |
| 15th Oct | Winchester City 3 - 1 Didcot Town | Neighbour, Jenkinson, Feeney |
| 11th Oct | Petersfield Town 1 - 3 Winchester City (FA Trophy) | Briggs, Wilson, Ford |
| 8th Oct | Winchester City 1 - 1 Petersfield Town (FA Trophy) | Matthews |
| 4th Oct | AFC Totton 2 - 3 Winchester City (League Cup) | Jenkinson (2), Wilson |
| 1st Oct | Harrow Borough 2 -1 Winchester City (FA Cup) | Neighbour |
| 27th Sept | Wantage Town 0 - 1 Winchester City | Feeney |
| 24th Sept | Winchester City 4 - 1 Bridgwater Town | Neighbour (2), Green (2) |
| 21st Sept | Winchester City 6 - 0 Blackfield & Langley (HSC) | Wilson (3), Neighbour (2), Briggs |
| 17th Sept | Winchester City 4 - 0 Truro City (FA Cup) | Feeney (2), Briggs, Neighbour |
| 10th Sept | Winchester City 0 - 2 Hereford | |
| 3rd Sept | Winchester City 4 - 2 Street (FA Cup) | Briggs, Bottomley, Neighbour, Feeney |
| 29th Aug | Wimborne Town 2 - 2 Winchester City | Green, Neighbour |
| 27th Aug | Winchester City 0 - 4 Tiverton Town | |
| 20th Aug | US Portsmouth 0 - 3 Winchester City (FA Cup) | Feeney (3) |
| 17th Aug | Didcot Town 4 - 0 Winchester City | |
| 13th Aug | Winchester City 0 - 2 Mangotsfield United | |
| 10th Aug | Winchester City 4 - 2 Salisbury | Barron, Briggs, Neighbour, Bottomley |
| 6th Aug | Slimbridge 5 -3 Winchester City | Flooks, Briggs, Feeney |
