| Date | Match |
|---|---|
| 12/08/23 | Market Drayton 2-0 Winsford United |
| 15/08/23 | Winsford United 0-3 Stafford Town |
| 19/08/23 | Winsford United 1-4 Stockport Town |
| 22/08/23 | Ashville 3-0 Winsford United |
| 26/08/23 | Armthorpe Welf 2-2 Winsford United |
| 28/08/23 | Winsford United 0-1 Maine Road |
| 02/09/23 | Stkprt Georgians 2-0 Winsford United |
| 05/09/23 | Winsford United 1-3 Droylsden |
| 09/09/23 | Winsford United 1-2 Sandbach United * |
| 16/09/23 | New Mills 1-5 Winsford United |
| 23/09/23 | Stafford Town 2-7 Winsford United |
| 30/09/23 | Winsford United 2-3 Abbey Hey |
| 07/10/23 | Winsford United 4-1 Abbey Hulton Utd |
| 10/10/23 | Abbey Hulton Utd 1-5 Winsford United |
| 14/10/23 | Winsford United 2-0 Eccleshall |
| 17/10/23 | Winsford United 0-1 Chadderton |
| 28/10/23 | Winsford United 1-2 Stkprt Georgians |
| 31/10/23 | Stalybridge Cel 4-3 Winsford United * |
| 04/11/23 | Droylsden 2-1 Winsford United |
| 11/11/23 | Winsford United 6-0 Market Drayton |
* Indicates appearance as a substitute
| Comp | Team | App |
|---|---|---|
| The Isuzu FA Vase | Winsford United | 1 |
| The Macron Cup | Winsford United | 1 |
| The Edward Case Cup | Winsford United | 2 |
| Cheshire Senior Cup | Winsford United | 1 |
| First Division South | Winsford United | 15 |
| Comp | YC | SB | RC |
|---|---|---|---|
| First Division South | 4 | 0 | 0 |
