Wakering entered 2 teams into the EWFL Prostate Cup 14 July 2019. Both A and B squads remained unbeaten throughout the competition. The B squad progressed to the final in which they met Leyton Orient who they had already beaten in the earlier rounds 3-1. It was clear that Orient had no answer to Wakering’s passing game so put up a stonewall defence to ensure that the final went to penalties, being their only chance of success. The match finished 0-0 although Wakering totally dominated creating multiple chances but could not find a way through a 6 man defence and so went into penalties. Wakering missed both their penalties and with Orient converting both theirs became the winners of the 2019 Prostate Cup.