As Manchester City and Watford prepare to kick-off this year’s Emirates FA Cup Final at Wembley Stadium, we take a look at a dozen of Boro’s most memorable days in the competition.
1970: Boro 1 Manchester United 1
After beating a West Ham side containing England World Cup heroes Bobby Moore, Martin Peters and Geoff Hurst, Boro came up against a now legendary Red Devils team including European Cup heroes Bobby Charlton and George Best - and matched them stride for stride.
Carlo Sartori gave United the lead before John Hickton equalised for Boro with a delightful chip to earn a deserved replay at Old Trafford.
United would win that replay on home turf, though Boro would get some revenge (it was just one of ten Boro cup ties with United in the space of five years) with FA Cup victory a year later thanks to goals from Hugh McIlmoyle and Derrick Downing.
1975: Boro 3 Sunderland 1
Jack Charlton’s Boro side were a force to be reckoned with having won the Second Division by a record points total the previous season.
A jam-packed Ayresome Park - 39,400, our highest home attendance in the last half century - watched as two goals from Hickton and one from Bobby Murdoch gave Boro this derby-day victory in front of the Match of the Day cameras.
Many believed The Teessiders could have a serious tilt at the trophy that year, but our FA Cup run came to an end away to Birmingham City in the quarter finals.
1977: Boro 4 Arsenal 1
Perhaps not the upset it would be in today’s game - we were three Division One places ahead of Arsenal in fifth at the time - this emphatic victory remained a big deal for an increasingly impressive Boro side chasing silverware.
David Mills was the home team’s hero, following up David Armstrong’s opener with a hat-trick that got Boro fans dreaming.
Another FA Cup quarter final defeat, this time to the imperious Liverpool, would spell the end of Chalton’s Boro tenure.
1981: Swansea City 0 Boro 5
Another one in front of TV, many fancied the high-flying second-tier Swans against John Neal’s out-of-sorts Boro.
In a show of clinical finishing, the Teessiders smashed five goals and were triumphant at the Vetch Field, Terry Cochrane adding a flourish with a superb overhead kick that would feature on the MOTD titles the next season.
Again, Boro were a fancied shout for FA Cup as we made our way into the latter stages of the cup competition, although this time Wolves were the villains as we once more fell at the quarter final hurdle.
And sadly, it signalled the break up of a young and talented Teessiders team, with hard times on the horizon.
1988: Boro 2 Everton 2
If previous match on this list was the end of an era, this cup clash with Division One heavyweights Everton signalled a revitalised Boro side very much on the up. Bruce Rioch's Boro side were Division Two newcomers, and had surprised many with a 1-1 draw at Goodison Park against the reigning league champions.
In this replay, Watson gave Everton the lead and with the game seemingly over, Boro skipper Tony Mowbray popped up to score a dramatic last-minute equaliser. When Alan Kernaghan scored nine minutes into extra time it looked as though Boro were on the verge of a major upset, but Everton hit back to make it 2-2 with the last kick of the game.
The tie went to a second replay at Goodison Park the following midweek, and after Stuart Ripley cancelled out another Sharp effort, the outcome was settled seven minutes from time when Mowbray put through his own goal.
Remarkably, there would be another FA Cup triple-header with Everton for Boro just two years later. After a stalemate at Ayresome and a 1-1 draw punctuated by a wonderful bullet striker from former Toffees trainee Gary Parkinson on his birthday at Goodison, Everton won at the third time as asking thanks to a goal from Norman Whiteside.
1997: Derby County 0 Boro 2
Worthy of inclusion simply for being the end of a big Boro hoodoo as we finally broke the FA Cup quarter final barrier - in our seventh post-war attempt.
Our biggest FA Cup win of modern times, 6-0 against Chester City, had began a fairytale cup run, with victories against Hednesford Town and Manchester City to follow.
Juninho, who had scored the winner against City in the previous round, scored a virtuoso opening goal before Fabrizio Ravanelli wrapped it up in the game’s final minutes.
1997: Boro 3 Chesterfield 3
The FA Cup is notorious for giant killings, and while Boro have no shortage of major scalps in our history, this cup classic saw us very nearly written into infamy ourselves.
Third tier Chesterfield took us all the way, Vladimir Kinder’s early red card setting the tone and the Spireites building a two-goal lead. Boro struck back to level things up, and Gianluca Festa put us into the lead for the first time when he scored in extra time, but Chesterfield had the final say with Jamie Hewitt putting his side back on equal footing with minutes to play.
Thankfully, Boro’s superiority would shine through in the replay to earn a first FA Cup final appearance…
1997: Chelsea 2 Boro 0
The only Boro defeat to make our list, but noteworthy as our first and as yet only FA Cup final.
Roberto Di Matteo struck within seconds under the Twin Towers and Eddie Newton made it two for The Blues late on, Boro dealt another hammer blow after relegation and defeat to Leicester in the Coca Cola Cup final.
Sandwiched between the Zenith Data Systems Cup final, our first Wembley outing, at the start of the decade and another Coca Cola Cup final defeat less than a year later, Chelsea were becoming all-too familiar foes on the biggest stage.
Nevertheless, a day that will live long in the memories of the Boro faithful.
2002: Boro 2 Manchester United 0
Noel Whelan and Andy Campbell took advantage of some uncharacteristically slack United defending to give Boro victory over Sir Alex Ferguson’s side in this fourth round tie.
Robbie Mustoe twice cleared off the line before Boro took control of this one, as Steve McClaren got one over his old mentor.
Boro would breeze past Blackburn Rovers and Everton in the next two rounds at the Riverside, and could count ourselves extremely unlucky to bow out to Arsenal in what was our second FA Cup semi-final appearance at Old Trafford. Despite dominating long periods of play against Arsene Wenger’s men, the match was decided by a fluke own goal from Gianluca Festa.
2006: Boro 4 Charlton Athletic 2
The games were piling up for Boro as the club competed on four fronts in the 2005/06 season. Having battled to earn a goalless quarter final draw with Charlton, we showed no sign of fatigue as the Addicks came to Teesside for the replay.
A 30-yard Fabio Rochemback free-kick put Boro ahead, and James Morrison restored our lead inside the first half-hour after a goal from Charlton’s Chris Perry. Three more goals flew in in a second half flurry of action, our front two of Hasselbaink and Viduka netting to book a place in the final four of the contest.
The semi-final with West Ham at Villa Park would not prove to be another success story for Boro, Marlon Harewood scoring the only goal for the Hammers and defender Chris Riggott spurning Boro’s best chance at salvaging an equaliser.
But Riggott was on the scoresheet as Boro overturned the semi final deficit set by Steaua Bucharest in the UEFA Cup just days earlier. West Ham, meanwhile, went on to stage one of the great cup finals against Liverpool.
2012: Sunderland 1 Boro 1
A chink of light in an otherwise difficult spell for the club in the wake of relegation from the top tier, this FA Cup trip to the Stadium of Light was one to once again capture the imagination of fans on Teesside.
Barry Robson put Championship Boro ahead on the day with a splendid volley against our top-tier hosts, with Frazier Campbell replying for the Black Cats. A replay would follow, and it took an extra time strike from Stephane Sessegnon to decide it in Sunderland’s favour.
Despite the gap in league standings, our North East neighbours were becoming a regular cup opponent, and Boro would prevail in a League Cup tie between the two later the same year.
2015: Manchester City 0 Boro 2
Quite simply a modern cup classic for Middlesbrough.
Few neutrals gave us a chance travelling to the Etihad to face Manuel Pellegrini’s league champions City in the fourth round.
Plucky Boro upset the odds, goals from Patrick Bamford and Kike just desserts for a masterful away performance. Another away day at Arsenal proved a step too far for Aitor Karanka’s side, but Wembley did lie in wait that season for a Boro side now brimming with confidence…