In 1882 Market Harborough became the first Leicestershire football club to enter an Association Football competition – Wellingborough Challenge Cup – which over time became referred to as the Northamptonshire Senior Cup – which is still contested annually. Unfortunately, the only information currently known about this momentous milestone in Leicestershire football history is that they were beaten in the opening round by Rushden. The following year in the same competition Market Harborough were slaughtered 10-0 by Wellingborough, but in March 1885 they reached the final – achieving another county footballing first. A ‘football special train’ conveyed 80 supporters from Harborough to witness the Wellingborough Challenge Cup Final against Rushden at Wellingborough. “Harborough won the toss, and elected to kick with the sun and wind, Rushden kicking off punctually at 3.30.Rushden then ran the ball up; and a good shot at goal was saved by Weldon, but immediately afterwards Chettle kicked the first goal for Rushden. Harborough for some time afterwards had the best of it, but Rushden got the ball in front of the Harborough goal, when “hands” were claimed by the latter, but not allowed, and a second goal, accidentally knocked through by Smith (Harborough) was scored for Rushden. Harborough afterwards secured a corner, but no score resulted, and the Harborough team began to play rather loosely, a number of “mulls” being made by several of the players. Rushden played well together, and having secured two more goals remained the victors by four goals to nil. The following comprised the Harborough team: — Messrs. C. B. Fisher (captain), F. R. Smith, H. G. Coales, J. L. Douglass, C. Burditt, R. M. Weldon, R. Howett, A. Moore, T. Underwood, and C. Lawrence.” [Leicester Chronicle – 14 March 1885].