Boro came out on top in the Championship thanks to an early Marcus Tavernier strike in November 2017 but will things be different now that Tony Pulis and Chris Coleman are in charge at the two North-East clubs?
Boro settling in to life under Pulis
Middlesbrough have acclimatised relatively well to life under their new boss so far, with their home defeat to Aston Villa eclipsed by two wins over Bolton Wanderers and Preston North End.
Boro fans saw a glimpse of life under Pulis at Deepdale as centre-back Daniel Ayala netted twice to secure a 3-2 win, a theme fans would do doubt be pleased to see continue as Boro mount a challenge for the play-offs.
Boro's defensive game has let them down on more than one occasion this season and after steadying the ship at Stoke, Crystal Palace and West Brom to name a few they certainly have the right man in Pulis to rectify those errors.
Fans may remember that the two have met twice in the FA Cup in recent years, with then-Premier League Sunderland coming out on top although it took a replay and extra-time at the Riverside to decide the fourth-round tie.
Pulis told the Chronicle ahead of the tie that he has "always been a loyal supporter of the FA Cup" and "will be absolutely delighted" if his Boro side progress on Saturday, adding that "Sunderland are a great football club but Chris [Coleman] will need time to sort that club out."
Black Cats require something special to overcome injury crisis
To add to the fact that Sunderland are bottom of the Championship following last weekend's 1-0 home defeat to Barnsley, Coleman is without no less than 13 players ahead of Saturday's FA Cup clash with Darron Gibson the latest to visit the treatment table.
Form has been patchy for the Black Cats since the Welshman took over with a 0-0 draw away to Wolves and a 1-0 away to Nottingham Forest overshadowed by poor home performances, seeing them held to a 1-1 draw by 10 man Birmingham and falling to defeats against Reading and Barnsley.
Sunderland do perform to a higher standard away from home with the pressure on their opposition however, so Pulis' men will be in for a tight affair that could be decided by a single goal.
Top scorer and main creative threat Lewis Grabban and Aiden McGeady are just two of the 13 out injured for the clash, so Coleman may have to turn to teenagers Josh Maja and Joel Asoro from the first whistle rather than using them as late substitutes as he has done in recent weeks.
Coleman told the Chronicle ahead of Saturday's game "we need to ensure we do the best we can with the squad of players we have" with Sunderland low on transfer funds, adding "we have to be as positive as we can and that comes from me".
Pulis will likely use Saturday's game as an opportunity to shuffle his pack with Dael Fry, Marcus Johnson, Adam Forshaw and Ashley Fletcher some of the fringe players who could be involved.
Boro have no major injury concerns although Adam Clayton, Martin Braithwaite and Forshaw have knocks and will be assessed closer to kick-off.
Sunderland are without a whole host of first-team players with Didier Ndong, McGeady, Grabban and Gibson the latest to be added to the injury list.
Lee Cattermole, Duncan Watmore, Marc Wilson, Billy Jones, Adam Matthews, Jonny Williams, Jack Rodwell and Lynden Gooch are all nursing injuries of various lengths and will not be involved, while Paddy McNair could make a late claim to be involved.
Middlesbrough (4-4-2): Konstantopoulos; Friend, Fry, Gibson, Christie; Downing, Johnson, Forshaw, Braithwaite; Fletcher, Gestede.
Sunderland (4-5-1): Steele; Oviedo, O'Shea, Browning, Love; Embleton, Honeyman, McNair, McManaman, Asoro; Vaughan.