Thames Ironworks lost their first fixture in the Southern League Division One 1–0 away at Reading on 16 September 1899, but managed their biggest league win of the season only two days later with 4–0 home win against Chatham. The game included two goals apiece for inside-forwards Albert Carnelly and new signing Kenny McKay. The Irons kept up their form for the FA Cup beating the amateur side, Royal Engineers at home 6–0 on 23 September, with a hat-trick from Bill Joyce, and a goal each from McKay, Roddy McEachrane and Jimmy Reid. A week later, Thames Ironworks featured in the next qualifying round of the FA Cup, this time beating Grays United 4–0 away, with goals from Joyce, McKay, Carnelly and centre-half Peter McManus.