| Date | Division | Match | String | Opponent | Result |
| 20/09/2018 | Div 4 South West | Brook Hotels 1 v Heswall 5 | 5 | Chris Brown | Won 3-1 |
| 27/09/2018 | Div 4 South West | Heswall 5 v Mollington Banastre 1 | 4 | James Kalahar | Won 3-1 |
| 04/10/2018 | Div 4 South West | Chester Rugby 3 v Heswall 5 | 5 | Wayne Lawrence | Lost 1-3 |
| 18/10/2018 | Div 4 South West | Barnton CC 2 v Heswall 4 | 5 | Nick Davies | Won 3-1 |
| 25/10/2018 | Div 4 South West | Moss Farm 1 v Heswall 5 | 4 | Mandy Beeston | Lost 1-3 |
| 01/11/2018 | Div 4 South West | Heswall 5 v Alsager 2 | 4 | Ian Turpin | Lost 0-3 |
| 08/11/2018 | Div 4 South West | Knutsford Sports 2 v Heswall 5 | 4 | Charles Keeble | Lost 0-3 |
| 15/11/2018 | Div 5 South West | Heswall 6 v Chester Rugby 4 | 2 | Wayne Lawrence | Lost 1-3 |
| 22/11/2018 | Div 4 South West | Heswall 4 v Heswall 5 | 4 | Matt Stapledon | Lost 1-3 |
| 29/11/2018 | Div 4 South West | Heswall 5 v Neston 3 | 3 | Andrew Ivey | Won 3-1 |
| 06/12/2018 | Div 4 South West | Barnton CC 2 v Heswall 5 | 1 | Eric Southern | Lost 1-3 |
| 13/12/2018 | Div 4 South West | Heswall 5 v Tattenhall 2 | 1 | George Dobson | Lost 0-3 |
| 03/01/2019 | Div 4 South West | Heswall 5 v Brook Hotels 1 | 4 | John Ellson | Won 3-2 |
| 10/01/2019 | Div 4 South West | Mollington Banastre 1 v Heswall 5 | 2 | Steve Meredith | Lost 0-3 |
| 07/02/2019 | Div 4 South West | Heswall 5 v Moss Farm 1 | 2 | Chris Sharpes | Lost 0-3 |
| 28/02/2019 | Div 4 South West | Heswall 5 v Knutsford Sports 2 | 1 | Graham Woods | Lost 0-3 |
| 07/03/2019 | Div 4 South West | Whitby 1 v Heswall 5 | 3 | Tom Maloney | Lost 1-3 |
| 14/03/2019 | Div 4 South West | Heswall 5 v Heswall 4 | 4 | John Dunne | Lost 0-3 |
| 21/03/2019 | Div 4 South West | Neston 3 v Heswall 5 | 4 | Jim Anderson | Won 3-1 |
| 28/03/2019 | Div 4 South West | Heswall 5 v Barnton CC 2 | 3 | Adam Evanson | Lost 0-3 |
