During the club's early years, they rapidly gained a reputation as the best team in Wiltshire. They lived up to this reputation when the Wiltshire Senior Cup competition began in the 1886/87 season - winning the trophy for the first six years it was played, and even having both the senior and reserve teams in the final for two seasons running! Indeed, when the trophy was won by Swindon Athletic in 1893, it was actually the Town reserves playing under a different name.
After entering the Southern League in 1894, the Wiltshire Cup became less important, and Swindon only won the trophy three times since, and once being shared between the reserve team and Trowbridge. The competition is still played to this day by Wiltshire's amateur sides.
In 1927, the Wiltshire Premier Shield was inaugurated, and it is this competition which is now seen as Wiltshire's major cup competition. Swindon have mainly fielded reserve sides in this competition, but nevertheless have won the trophy 27 times up until 1992. The club then decided to take a break from the competition, but have since started to enter again, fielding young reserve sides since 2000/2001.