| 1 | Sat 11 Aug 2018 | 142-0 v Chalfont St PeterChalfont St Peter 0-2 Chipstead |
| 2 | Mon 27 Aug 2018 | 91-3 v Tooting & Mitcham UnitedTooting & Mitcham United 3-1 Chipstead |
| 3 | Sat 1 Sep 2018 | 73-4 v Bedfont SportsChipstead 3-4 Bedfont Sports |
| 4 | Sat 15 Sep 2018 | 110-0 v Hanwell TownHanwell Town 0-0 Chipstead |
| 5 | Tue 25 Sep 2018 | 111-0 v South ParkSouth Park 0-1 Chipstead |
| 6 | Sat 29 Sep 2018 | 110-3 v WestfieldChipstead 0-3 Westfield |
| 7 | Sat 6 Oct 2018 | 95-0 v FC RomaniaFC Romania 0-5 Chipstead |
| 8 | Tue 16 Oct 2018 | 95-0 v Egham TownChipstead 5-0 Egham Town |
| 9 | Sat 20 Oct 2018 | 92-0 v Waltham AbbeyChipstead 2-0 Waltham Abbey |
| 10 | Sat 3 Nov 2018 | 90-4 v MarlowMarlow 4-0 Chipstead |
| 11 | Sat 17 Nov 2018 | 93-3 v CheshuntCheshunt 3-3 Chipstead |
| 12 | Sat 24 Nov 2018 | 92-3 v NorthwoodChipstead 2-3 Northwood |
| 13 | Sat 1 Dec 2018 | 93-3 v WareWare 3-3 Chipstead |
| 14 | Tue 4 Dec 2018 | 93-2 v UxbridgeChipstead 3-2 Uxbridge |
| 15 | Sat 8 Dec 2018 | 92-5 v Hertford TownHertford Town 5-2 Chipstead |
| 16 | Sat 22 Dec 2018 | 91-3 v Tooting & Mitcham UnitedChipstead 1-3 Tooting & Mitcham United |
| 17 | Sat 5 Jan 2019 | 120-3 v Bracknell TownChipstead 0-3 Bracknell Town |
| 18 | Tue 8 Jan 2019 | 111-2 v Hayes & Yeading UnitedChipstead 1-2 Hayes & Yeading United |
| 19 | Sat 12 Jan 2019 | 90-1 v Bedfont SportsBedfont Sports 1-0 Chipstead |
| 20 | Sat 19 Jan 2019 | 90-2 v WestfieldWestfield 2-0 Chipstead |
| 21 | Sat 26 Jan 2019 | 92-1 v FC RomaniaChipstead 2-1 FC Romania |
| 22 | Sat 2 Feb 2019 | 93-0 v Waltham AbbeyWaltham Abbey 0-3 Chipstead |
| 23 | Tue 5 Feb 2019 | 161-4 v South ParkChipstead 1-4 South Park |
| 24 | Sat 9 Feb 2019 | 93-2 v Chalfont St PeterChipstead 3-2 Chalfont St Peter |
| 25 | Sat 16 Feb 2019 | 90-0 v Ashford Town (Middx)Ashford Town (Middx) 0-0 Chipstead |
| 26 | Sat 23 Feb 2019 | 91-0 v MarlowChipstead 1-0 Marlow |
| 27 | Sat 2 Mar 2019 | 92-1 v UxbridgeUxbridge 1-2 Chipstead |
| 28 | Sat 9 Mar 2019 | 90-1 v CheshuntChipstead 0-1 Cheshunt |
| 29 | Sat 16 Mar 2019 | 90-2 v NorthwoodNorthwood 2-0 Chipstead |
| 30 | Sat 23 Mar 2019 | 91-3 v WareChipstead 1-3 Ware |
| 31 | Sat 30 Mar 2019 | 90-0 v Hertford TownChipstead 0-0 Hertford Town |
| 32 | Sat 6 Apr 2019 | 110-1 v Hayes & Yeading UnitedHayes & Yeading United 1-0 Chipstead |
| 33 | Sat 13 Apr 2019 | 90-1 v Hanwell TownChipstead 0-1 Hanwell Town |
| 34 | Sat 20 Apr 2019 | 90-1 v Bracknell TownBracknell Town 1-0 Chipstead |
| 35 | Mon 22 Apr 2019 | 100-0 v MoleseyChipstead 0-0 Molesey |
| 36 | Sat 27 Apr 2019 | 94-1 v Egham TownEgham Town 1-4 Chipstead |
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