Worksop first entered the English Cup, as it was then known in the 1893-94 season, when the home ground was at Bridge Meadow on Newcastle Avenue, and the club were playing in the Sheffield & Hallamshire League.
The draw for the 1st Qualifying Round brought Rotherham Town to Worksop’s homely enclosure and drew a 2,000 strong crowd.
Rotherham, then in the 2nd Division of the Football League were expected to sail through, but the Worksop lads, playing in Black & White quartered shirts, the racing colours of the Duke of Portland, fought out an unexpected 3-2 victory.
A trip to play fellow Sheffield League side Wath-upon-Dearne was the reward from this epic win.
Spurred on by the acclaim from their efforts in the 1st Qualifying Round, Worksop again won through, this time winning 3-1, after extra-time. A crowd of 500 fans greeted the returning team at the Railway station and marched behind the town band to the Market Place.
The 3rd Qualifying Round draw brought the mighty Gainsborough Trinity to town. Gainsborough had been early rivals in the days of friendly, or “ordinary” matches as they were known, but it had been some years since the teams had met as equals. Another 2000 strong crowd assembled at the “Meadow”. Sissons opened the scoring for Worksop but Trinity hit back twice to lead 2-1. Copestake levelled, but Trinity got the winner with just three minutes left on the clock to seal a dramatic win