The other, Raith Rovers, was elected to the Scottish League in 1902, which immediately made the prospects of another senior club surviving in the town much more difficult.

[5] In the second round, at home to First Leaguers Partick Thistle, the United held out until a quarter of an hour to go, including withstanding a missed penalty, when Gray scored the only goal of the game; the United was handicapped by regular goalkeeper Dorward being injured before the match and Young, a junior at Vale of Wemyss, stepped in.

It won the 8-team Fife Cup for the first time, beating Cowdenbeath 3–1 in the final at Stark's Park in front of 2,160 people;[9] the strength of the tournament being demonstrated by each of the other teams being Scottish League members present or future.

The United had finished its fixtures one point clear of Dundee, who had not been able to play the newly-defunct Hearts of Beath; after expunging all fixtures, the United and Dundee were level on points, and the Fifeshire FA agreed to award the title jointly to the pair.

Possibly as a result of this success, Raith Rovers proposed a merger of the two Kirkcaldy sides in 1908, but it did not proceed.