Woking began their ENL Cup campaign with a 2-1 comeback victory over Southampton U21 on September 17, 2025. The National League side showed great character to overturn a deficit and secure a winning start against category one academy opposition. Southampton's talented youngsters started brightly, taking an early lead that reflected their sharpness in possession. Woking, however, grew into the game and found an equalizer before halftime, changing the complexion of the match. The second half was a more even affair, with both teams creating chances. The winner for Woking came in the latter stages, a reward for their persistent pressure and tactical discipline. The 2-1 final score provided a morale-boosting win for Woking and three valuable points in the group standings. This match result demonstrated the competitive balance in the ENL Cup, where experienced non-league sides can overcome talented youth teams.