It has been 25 years since Middlesbrough faced off with Sheffield Wednesday in the FA Cup. Boro came away from Hillsborough with a 2-1 victory in 1992.
The sides have played more recently when they were in the Championship last season and the three seasons prior to Boro's promotion-winning campaign.
Despite doing the double over the Owls last season, Middlesbrough won only one of their previous six meetings.
The most recent Riverside fixture saw Aitor Karanka's men run out 1-0 victors thanks to a first-minute effort from Cristhian Stuani.
Chances could be given to 'fringe players'
It has been noted by some that Karanka has been exclusive in his first season as a Premier League manager and once players have disappointed him, he has been slow to give them another opportunity in the side.
The cup match could, therefore, see players such as Emilio Nsue and Daniel Ayala play for the first time in months.
Other players who haven't seen much game time in recent weeks include big money signings from last season Stewart Downing and Jordan Rhodes.
Rhodes looks to be on his way out of Middlesbrough having started only two games in the Premier League this season, and the arrival of former teammate Rudy Gestede has done nothing to halt these rumours.
Gestede arrived from Aston Villa for £6 million earlier in the week, but is unlikely to feature against Sheffield Wednesday.
It would be surprising to see Alvaro Negredo start in the FA Cup; the Spanish striker played 90 minutes on the 31st of December and 2nd of January in the Premier League fixtures.
A possible double-edged-sword for Boro
In recent years, Middlesbrough have had good cup runs, including visits to Anfield and the Emirates.
This time, however, having a congested fixture list could be problematic for Boro's hopes of survival.
More games could mean fatigue or injury for some of Aitor Karanka's star players and that could have a detrimental effect on Boro staying up.
A less congested fixture list, however, did not affect Middlesbrough's early season.
Fulham knocked Middlesbrough out of the EFL Cup in the first round, and there was no significant boost to Boro's form after losing at Craven Cottage.