In the 1906–07 season the club entered the North-West Junior League. Their first ever junior match was a league match away to Farm Wanderers which ended in a 4–4 draw. In the season of 1907–08, Billy Gillespie began playing for the club, and went on to become one of the club's greatest ever players. The club won the North-West Charity Cup that season, beating Derry Celtic Wanderers 4–1 in the final, making them the first Junior team ever to win the trophy. Mr William Logue became chairman of the club and remained chairman until the year 1914.