The club was formed in 1877 and took its name from the district of
Cunninghame. The club's name was often given as
Stewarton Cunningham or simply
Stewarton. It first played competitive football in the 1879–80 season when it entered the
Ayrshire Cup, reaching the third round. Its best run in the competition came in 1881–82, when it reached the fourth round. The club made its debut in the
Scottish Cup in
1879–80, losing 6–1 to
Maybole Ladywell in the second round, a protest against encroachment getting short shrift. After a withdrawal, the club returned in
1881–82 by losing 9–0 at
Portland, and the next year suffered a 5–3 home defeat to
Ayr. After losing Scottish Cup ties in
1883–84 and
1884–85 to
Kilmarnock Athletic by 9–1 and 14–0 respectively, and 9–1 in the Ayrshire Cup to
Mauchline in the latter year, the club left Senior football to become a member of the
Scottish Junior Football Association, which made it ineligible to play in the Scottish Cup or the Ayrshire Cup. The club reverted to Senior status in 1887, and seemingly reached the semi-final of the Ayrshire Cup with a 2–0 win over
Annbank in 1887–88; however, after a protest "on account of the ground not being in good order", Annbank won the replayed tie 3–1, to the "great dissatisfaction" of the "little town". On its first entry back into the Scottish Cup in
1888–89, Cunninghame registered its only win in the main competition, 4–3 against the new
Rosebank club of
Kilmarnock, the match marking Rosebank's "first bow to a football crowd of any size"; Stewarton had been drawn away, but Rosebank's Holm Quarry ground had already been booked for a cricket match. The rise of professionalism left the Bonnet Makers behind, and after two disastrous defeats in 1891–92 - 14–0 at home to
Kilmarnock in the Ayrshire Cup, and 9–0 at
Dalry in the qualifying rounds of the Scottish Cup - it returned to the Junior game. The club's greatest success in the Junior ranks was winning the Ayrshire Junior League in 1900–01, after a 5–1 play-off victory over the Afton Lads club. However the club left the competition before the 1904–05 season. ==Colours==