[4] The club effectively inherited the Old St Paul's place in the FA Cup so entered the qualifying rounds for the first time, and, after its scheduled opponents from the Crystal Palace School of Engineers admitted it had entered by accident and scratched,[5] was humbled 8–0 by the Old Carthusians in the second.

[7] From 1891, London clubs such as Woolwich Arsenal and Millwall Rovers started to turn professional, and the Ramblers were left behind.

The club did not enter the Cup in 1891–92, but in 1892–93 gained its first win in the competition, beating Old Cranleighans 5–1 in the first round; the professionals of Woolwich Arsenal scored double figures against the Ramblers in the second.

Even at the FA Amateur Cup level the club struggled - it lost 6–1 at Tottenham Hotspur in the second round in 1894–95.

[10] The last season for the club was 1895–96, in which it lost 1–0 to Maidenhead in the first qualifying round of the FA Cup (despite Maidenhead starting with 9 men because of a train problem),[11] and finished the season losing to Wolverton in the semi-final of the Wolverton Charity Cup - both sides were reduced to 10 men due to sendings-off for foul play.