[3] The club first played in the Perthshire Cup in the 1885–86 season, but struggled in its early years, on occasion going into abeyance due to the recruitment of its better players to better clubs, most notably Fair City Athletic, which persuaded the McLaren brothers, Barclay, Kinnoch, and Condie to switch allegiance in the 1880s and 1890s.

The second occasion was 1906–07, a 3–1 defeat to Forfar Athletic ending the club's run in the third round; Tulloch was 2–0 down inside ten minutes and had Mailer in goal to thank for keeping the score reasonable.

[10] The club gained a notable result in 1910–11 by holding St Johnstone to a draw in the first round, even earning a half-time lead,[11] but lost the replay after centre-half Robinson had to withdraw from the tie due to a clashing cricket commitment.

The first occasion (in 1903–04) was after the club finished up its fixtures before closest rivals Duncrub Park, leaving Auld Dinnin' the task of forcing a championship play-off by winning the final two matches;[13] however Park drew its last fixture with Stanley and Tulloch took its first trophy.

[16] Tulloch also won the first Perthshire Consolation Cup in 1905–06, for clubs eliminated from the county competition before the final, with a 2–1 win over Vale of Atholl.