The first season was deemed a reasonable success with steady attendances to home games and progress in the FA Cup although the fluctuating nature of the team meant that consistency was never really achieved.

United eventually reached the second round proper of the FA Cup where they were comprehensively beaten by the more experienced Bolton Wanderers and finished the season having been accepted to play in the newly formed Midland Counties League the following term.

Their opponents were drawn both from the local area (Sheffield having a number of established teams at this time) and from further afield, particularly the North-West and West Midlands.

[3] The establishment of a new, well-financed, football team in the city had caused some consternation amongst the local FA[4] and United undertook a low-key start, not playing their first game at Bramall Lane until the end of September, against Birmingham St.

[3] The team continued their campaign of friendly fixtures into 1890, with varying degrees of success, whilst competing in the FA Cup for the first time.

[4] They represented United's first reported entry into the transfer market, arriving for a combined fee of £200, and signalled a new era of full professionalism for the club.

Giving up home advantage in return for a payment of £40 (a practice that was actually against the rules of the competition) they travelled across the Pennines only to be trounced 13–0, a result that remains United's worst ever cup defeat.

United progressed through three early rounds of the Challenge Cup, beating Sheffield Exchange, Heeley and Attercliffe before facing Staveley at Bramall Lane in the semi-final.

United were held to a 0–0 draw in the first fixture at Bramall Lane but succumbed to a single goal in the return leg which was played at the ground of Rotherham Swifts.

[3] The Wharncliffe Cup was a smaller affair and The Blades needed only to beat Doncaster Rovers in a home game to progress to the semi-final.