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 having both the senior and reserve teams in the final for two seasons running! After the Senior side thrashed the Reserves by thirteen goals to nil in the final of 1892, the Club took a step back from the competition - paving the way for Swindon Town Athletic (STFC's amateur reserve team) to take the title in 1893! The run was finally broken in 1894, when Swindon Wanderers took the trophy for the first time, beating Calne in the final. Town sides went on to win the trophy in 1896 (the reserves jointly holding the trophy with Trowbridge), 1897, 1904, 1907, 1909 and 1920.
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.
Though the Wiltshire Cup continues to this day for amateur sides, and despite the trophy having seniority according to the Wiltshire FA, the Wiltshire Premier Shield is now seen as the county's main cup competition. The Premier Shield was inaugurated for the 1926/27 season, and in much the same vein as its predecessor, the Town dominated the early years of the competition - winning the trophy in its first seven seasons, and in fifteen of the twenty competitions played from 1927 to 1959. Swindon have mostly fielded reserve sides in this competition, but nevertheless won the trophy a total of 27 times up until 1992 before deciding to take a break from the competition - more recently, since 2000/01 the club has generally fielded young reserve sides, last winning the Premier Shield in 2010, thanks to a 2-1 final victory over Supermarine.
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