Chertsey Town x Winchester City se enfrentatam em 07/09/2024 (Non League Premier: Southern South) no Alwyns Lane Football Ground (Chertsey). Cartões: Nick Jupp (77'). placar final: 3 - 3.

Gosport Borough x Winchester City se enfrentatam em 11/09/2024 (Hampshire Senior Cup) no Privett Park (Gosport). Vitória do Winchester City, placar final: 0 - 2.

Winchester City x Hungerford Town se enfrentatam em 14/09/2024 (FA Cup) no The Denplan City Ground (Winchester). Empate entre Winchester City x Hungerford Town, placar final: 1 - 1.

Hungerford Town x Winchester City se enfrentatam em 17/09/2024 (FA Cup) no Bulpit Lane (Hungerford). Vitória do Winchester City, placar final: 0 - 1.

Tiverton Town x Winchester City se enfrentatam em 21/09/2024 (Non League Premier: Southern South) no Ladysmead (Tiverton). Derrota do Winchester City, placar final: 2 - 1.

Merthyr Town x Winchester City se enfrentatam em 24/09/2024 (Non League Premier: Southern South) no Penydarren Park (Merthyr Tydfil). Derrota do Winchester City, placar final: 3 - 1.

Winchester City x Weymouth se enfrentatam em 28/09/2024 (FA Cup) no The Denplan City Ground (Winchester). Empate entre Winchester City x Weymouth, placar final: 2 - 2.

Weymouth x Winchester City se enfrentatam em 01/10/2024 (FA Cup) no Bob Lucas Stadium (Weymouth). Derrota do Winchester City, placar final: 3 - 0.

Winchester City x Swindon Supermarine se enfrentatam em 05/10/2024 (Fa Trophy) no The Denplan City Ground (Winchester). Vitória do Winchester City, placar final: 5 - 2.

Winchester City x Poole Town se enfrentatam em 08/10/2024 (Non League Premier: Southern South) no The Denplan City Ground (Winchester). Empate entre Winchester City x Poole Town, placar final: 1 - 1.