Middlesbrough had been formed before Sunderland on 18 February 1876.
In 1887-88, the sides faced each other for the first time and with Sunderland challenging their opponents place at the top of the North-East soccer ladder the game in a qualifying round of the FA Cup was a fierce affair. Sunderland took a 2-0 half time lead only for Boro, playing at home, to storm back in the second period to earn a draw. The replay at Newcastle Road saw the away side pegged back as their 2-0 lead evaporated as Sunderland scored four times to win 4-2. The losing side was though to go through as they immediately protested about the appearance of three Scots - Monaghan, Hastings and Richardson - in the Sunderland side. The trio had appeared as professionals but the rules was that any professional not local to a team had to live no more than six miles away over a two-year period if they were to play in FA competitions. The three were suspended and Boro were awarded the tie.