The club was founded as Kirkcaldy Wanderers in 1881, playing its first match against Rossend of Burntisland on 12 November 1881, after practising for several weeks on "Mr Stark's park".

The club was given no chance against St Bernards in the third round, but the Saints only just squeezed home 2–1, Kirkcaldy having a goal disallowed for a prior foul.

Its last match in the main section was another tight run affair against a top Edinburgh side, a 4–3 defeat at home to Hibernian in 1890–91.

After twice beating Burntisland Thistle in the 1888–89 Fifeshire Cup (the first victory being annulled because of "non-registration of colours"),[13] the club withdrew from the competition, "as they consider - and perhaps rightly, too - that they have not been fairly dealt with by the Association".

[14] The club did not take part in the Fifeshire for the next three seasons, its competitive football coming in the Scottish Cup and the East of Scotland Shield.

This may have been a mistake, as in that period Raith Rovers, a younger club in the town, turned senior and continued its entries to the local cup.

The club however lost 6–2 to a strong Cowdenbeath side, having been 2–0 up as late as the 67th minute, but collapsing in the face of the Miners' "forcible tactics" and "remarkable stamina".

Even in that small competition, the club could not fulfil its fixtures - in 1896–97 it only played three matches, winning two and losing one to Hearts of Beath, going from 2–0 up to 3–2 down in three second-half minutes.