[6] The match was traditionally played on Hansel Monday, the first day of the New Year, and one Callander man, John Burns Connell, took a Hansel Monday ball to Glasgow in the 1860s to rent out for matches at Glasgow Green; Burns was later a player for the Thistle club, the Callander club made of up former Thistle players, and the Eastern F.C.

[7] The first association match recorded in Callander was the 1877–78 Scottish Cup second round tie between Grasshoppers and Clifton & Strathfillan, held at the Roman Camp, and which drew a large crowd.

[9] In 1878–79 it entered the Scottish Cup for the first time, beating Coupar Angus after a match of "give and take" character at the North Inch in Perth.

4–2 in the fourth round;[13] in the fifth however the club lost 12–0 at Thornliebank, who reached the competition's final, the Gregarachs unable to adapt their long-kicking style against a more 'scientific' side.

[15] The club had not been helped by apathy in the town,[16] but made a comeback to senior football in 1888, by entering the Perthshire Cup, and beating Vale of Ruthven 10–0 in the first round; Rob Roy offered the Auchterarder club a choice of half of the gate or a tea supper after the match - the visitors chose the money, "and left by the first train, having no doubt got enough of Callander".

Rob Roy therefore entered the Perthshire Cup again from 1890 onwards; it was outclassed in most of its entries, but reached the final in 1897–98, with one of the matches being a "great surprise" 4–0 victory against St Johnstone, thanks to long ball tactics on a heavy pitch, and two breakaway goals in the second half.

[19] St Johnstone protested after the match, on the basis that four of the Rob Roy players (Lynch, Harding, and Abbot of Glasgow, and Honeyman of Dunblane) were not bona fide club members.