| Petts Wood & Orpington 2 | 2 - 4 | Petts Wood & Orpington 1 | Fri 4th Oct 2019 | 19:45 | MET County / Lewis Cup | Kent League | LV |
| Petts Wood & Orpington 3 | 2 - 4 | Chislehurst 1 | Fri 11th Oct 2019 | 19:45 | MET Stevenson Cup | Kent League | LV |
| Petts Wood & Orpington 10 | 3 - 1 | Petts Wood & Orpington 8 | Fri 11th Oct 2019 | 19:45 | MET Intro Cup | Kent League | LV |
| Petts Wood & Orpington 1 | 2 - 4 | Petts Wood & Orpington 2 | Fri 18th Oct 2019 | 19:45 | MET County / Lewis Cup | Kent League | LV |
| Petts Wood & Orpington 9 | 3 - 1 | Petts Wood & Orpington 8 | Fri 25th Oct 2019 | 19:45 | MET Intro Cup | Kent League | LV |
| Petts Wood & Orpington 2 | 2½ - 3½ | Beckenham & Bromley 1 | Fri 1st Nov 2019 | 19:45 | MET County / Lewis Cup | Kent League | LV |
| Petts Wood & Orpington 8 | 2 - 2 | Gravesend 5 | Fri 1st Nov 2019 | 19:45 | MET Intro Cup | Kent League | LV |
| Petts Wood & Orpington 9 | 1½ - 2½ | Petts Wood & Orpington 10 | Fri 1st Nov 2019 | 19:45 | MET Intro Cup | Kent League | LV |
| Beckenham & Bromley 5 | ½ - 3½ | Petts Wood & Orpington 10 | Thu 7th Nov 2019 | 19:30 | MET Intro Cup | Kent League | LV |
| Petts Wood & Orpington 2 | 3 - 3 | Lewisham 1 | Fri 8th Nov 2019 | 19:45 | MET County / Lewis Cup | Kent League | LV |
| Petts Wood & Orpington 6 | 2½ - 1½ | Petts Wood & Orpington 7 | Fri 8th Nov 2019 | 19:45 | MET Tom Fuller Cup | Kent League | LV |
| Charlton 2 | 3 - 1 | Petts Wood & Orpington 6 | Mon 11th Nov 2019 | 19:45 | MET Tom Fuller Cup | Kent League | LV |
| Sidcup 3 | 1 - 5 | Petts Wood & Orpington 5 | Wed 13th Nov 2019 | 19:45 | MET Harvey Cup | Kent League | LV |
| Beckenham & Bromley 1 | 2½ - 3½ | Petts Wood & Orpington 1 | Thu 14th Nov 2019 | 19:30 | MET County / Lewis Cup | Kent League | LV |
| Petts Wood & Orpington 3 | 1½ - 4½ | Dartford & Swanley 1 | Fri 15th Nov 2019 | 19:45 | MET Stevenson Cup | Kent League | LU |
| Petts Wood & Orpington 8 | 1 - 3 | Lewisham 7 | Fri 15th Nov 2019 | 19:45 | MET Intro Cup | Kent League | LV |
| Lewisham 6 | ½ - 3½ | Petts Wood & Orpington 7 | Wed 20th Nov 2019 | 19:45 | MET Tom Fuller Cup | Kent League | LV |
| Petts Wood & Orpington 4 | 2 - 4 | Dartford & Swanley 2 | Fri 22nd Nov 2019 | 19:45 | MET En Passant Cup | Kent League | LV |
| Gravesend 2 | 4 - 2 | Petts Wood & Orpington 4 | Tue 26th Nov 2019 | 19:45 | MET En Passant Cup | Kent League | LV |
| Lewisham 7 | 2 - 2 | Petts Wood & Orpington 9 | Wed 27th Nov 2019 | 19:45 | MET Intro Cup | Kent League | LV |
| Petts Wood & Orpington 3 | 6 - 0 | Lewisham 2 | Fri 29th Nov 2019 | 19:45 | MET Stevenson Cup | Kent League | LU |
| Petts Wood & Orpington 8 | 3 - 1 | Sidcup 5 | Fri 29th Nov 2019 | 19:45 | MET Intro Cup | Kent League | LV |
| Dartford & Swanley 3 | 3½ - 2½ | Petts Wood & Orpington 5 | Thu 5th Dec 2019 | 19:45 | MET Harvey Cup | Kent League | LV |
| Beckenham & Bromley 5 | 1 - 3 | Petts Wood & Orpington 9 | Thu 9th Jan 2020 | 19:30 | MET Intro Cup | Kent League | LV |
| Petts Wood & Orpington 5 | 4 - 2 | Gravesend 3 | Fri 10th Jan 2020 | 19:45 | MET Harvey Cup | Kent League | LV |
| Gravesend 5 | 1 - 3 | Petts Wood & Orpington 9 | Tue 14th Jan 2020 | 19:45 | MET Intro Cup | Kent League | LV |
| Petts Wood & Orpington 4 | 2 - 4 | Beckenham & Bromley 2 | Fri 17th Jan 2020 | 19:45 | MET En Passant Cup | Kent League | LV |
| Petts Wood & Orpington 6 | 2 - 2 | Sidcup 4 | Fri 17th Jan 2020 | 19:45 | MET Tom Fuller Cup | Kent League | LV |
| Petts Wood & Orpington 8 | 4 - 0 | Beckenham & Bromley 5 | Fri 24th Jan 2020 | 19:45 | MET Intro Cup | Kent League | LV |
| Petts Wood & Orpington 10 | 3 - 1 | Sidcup 5 | Fri 24th Jan 2020 | 19:45 | MET Intro Cup | Kent League | LV |
| Beckenham & Bromley 3 | 3 - 3 | Petts Wood & Orpington 5 | Thu 30th Jan 2020 | 19:30 | MET Harvey Cup | Kent League | LV |
| Petts Wood & Orpington 4 | 4 - 2 | Sidcup 2 | Fri 31st Jan 2020 | 19:45 | MET En Passant Cup | Kent League | LV |
| Sidcup 1 | 2½ - 3½ | Petts Wood & Orpington 3 | Wed 5th Feb 2020 | 19:45 | MET Stevenson Cup | Kent League | LV |
| Sidcup 5 | 0 - 4 | Petts Wood & Orpington 9 | Wed 5th Feb 2020 | 19:45 | MET Intro Cup | Kent League | LV |
| Petts Wood & Orpington 1 | 3½ - 2½ | Lewisham 1 | Fri 7th Feb 2020 | 19:45 | MET County / Lewis Cup | Kent League | LV |
| Petts Wood & Orpington 6 | 1 - 3 | Lewisham 6 | Fri 7th Feb 2020 | 19:45 | MET Tom Fuller Cup | Kent League | LV |
| Beckenham & Bromley 4 | 2 - 2 | Petts Wood & Orpington 6 | Thu 13th Feb 2020 | 19:30 | MET Tom Fuller Cup | Kent League | LV |
| Petts Wood & Orpington 7 | 2 - 1½ | Charlton 2 | Fri 14th Feb 2020 | 19:45 | MET Tom Fuller Cup | Kent League | LV |
| Lewisham 3 | 1½ - 4½ | Petts Wood & Orpington 3 | Wed 19th Feb 2020 | 19:45 | MET Stevenson Cup | Kent League | LV |
| Lewisham 7 | 0 - 4 | Petts Wood & Orpington 10 | Wed 19th Feb 2020 | 19:45 | MET Intro Cup | Kent League | LV |
| Beckenham & Bromley 1 | 3½ - 2½ | Petts Wood & Orpington 2 | Thu 20th Feb 2020 | 19:30 | MET County / Lewis Cup | Kent League | LV |
| Petts Wood & Orpington 7 | 2 - 2 | Gravesend 4 | Fri 21st Feb 2020 | 19:45 | MET Tom Fuller Cup | Kent League | LV |
| Charlton 3 | 3 - 1 | Petts Wood & Orpington 8 | Mon 24th Feb 2020 | 19:45 | MET Intro Cup | Kent League | LV |
| Petts Wood & Orpington 4 | 3½ - 2½ | Lewisham 4 | Fri 28th Feb 2020 | 19:45 | MET En Passant Cup | Kent League | LV |
| Petts Wood & Orpington 6 | 3½ - ½ | Gravesend 4 | Fri 28th Feb 2020 | 19:45 | MET Tom Fuller Cup | Kent League | LV |
| Charlton 3 | 3 - 1 | Petts Wood & Orpington 9 | Mon 2nd Mar 2020 | 19:45 | MET Intro Cup | Kent League | LU |
| Petts Wood & Orpington 7 | 2 - 2 | Beckenham & Bromley 4 | Fri 6th Mar 2020 | 19:45 | MET Tom Fuller Cup | Kent League | LV |
| Charlton 1 | 3½ - 2½ | Petts Wood & Orpington 5 | Mon 9th Mar 2020 | 19:45 | MET Harvey Cup | Kent League | LV |
| Petts Wood & Orpington 3 | 3 - 3 | Gravesend 1 | Fri 13th Mar 2020 | 19:45 | MET Stevenson Cup | Kent League | LV |
| Petts Wood & Orpington 4 | 4½ - 1½ | Chislehurst 2 | Fri 13th Mar 2020 | 19:45 | MET En Passant Cup | Kent League | LV |
| Lewisham 5 | 0 - 0 | Petts Wood & Orpington 5 | Wed 18th Mar 2020 | 19:45 | MET Harvey Cup | Kent League | LU |
| Petts Wood & Orpington 1 | 0 - 0 | Beckenham & Bromley 1 | Fri 20th Mar 2020 | 19:45 | MET County / Lewis Cup | Kent League | LU |
| Petts Wood & Orpington 10 | 0 - 0 | Gravesend 5 | Fri 20th Mar 2020 | 19:45 | MET Intro Cup | Kent League | LU |
| Lewisham 1 | 0 - 0 | Petts Wood & Orpington 2 | Wed 25th Mar 2020 | 19:45 | MET County / Lewis Cup | Kent League | LU |
| Sidcup 4 | 0 - 0 | Petts Wood & Orpington 7 | Wed 25th Mar 2020 | 19:45 | MET Tom Fuller Cup | Kent League | LU |
| Petts Wood & Orpington 10 | 0 - 0 | Charlton 3 | Fri 27th Mar 2020 | 19:45 | MET Intro Cup | Kent League | LU |
| Lewisham 1 | 0 - 0 | Petts Wood & Orpington 1 | Wed 1st Apr 2020 | 19:45 | MET County / Lewis Cup | Kent League | LU |
| Maidenhead C | 0 - 0 | Petts Wood & Orpington A | Tue 27th Oct 2020 | 18:00 | Five Counties Div X | Five Counties Online League | OU |
