The draw for the First and Second rounds of the Sydenhams (Wessex) League Cup was made at the Annual General Meeting and is as follows:

AFC Stoneham v Alton
Alresford Town v Laverstock & Ford
Cowes Sports v Horndean
East Cowes Vics v New Milton Town
Fawley AFC v Lymington Town
Petersfield Town v Verwood Town
Romsey Town v Hamworthy United
Totton & Eling v Solent University

Amesbury Town v Petersfield Town/Verwood Town
Bashley v Baffins Milton Rovers
Bemerton Heath Harlequins v Andover Town
Bournemouth v Downton
Brockenhurst v East Cowes Vics/New Milton Town
Cowes Sports/Horndean v Newport IoW
Fareham Town v Christchurch
Hamble Club v Pewsey Vale
Hythe & Dibden v Ringwood Town
Portland United v Fleet Town
Romsey Town/Hamworthy United v Alresford Town/Laverstock & Ford
Shaftesbury v AFC Stoneham/Alton
Tadley Calleva v AFC Portchester
Totton & Eling/Solent University v Andover New Street
U.S. Portsmouth v Folland Sports
Whitchurch United v Fawley AFC/Lymington Town