Gareth Southgate, Gordon Strachan and Tony Mowbray fell by the wayside before Aitor Karanka took over on Teesside during a relegation fight in November 2013, and Boro have been on the up ever since.
Boro have taken on both Manchester clubs and beaten them in the last two seasons in the cups, while Liverpool needed penalties to get past them two seasons ago - but do they have what it takes to kick on and make sure their next top-flight stay will last more than one season?
From disaster to joy in 2015/16
The pain of a non-performance in the 2014/15 play-off final was a worry for Middlesbrough before the start of last season, but after a stuttering start to the campaign they looked unstoppable by the turn of the season.
With a points buffer at the top and two games in hand over their nearest rivals, it was their title to lose, but a mid-season meltdown and some shock defeats saw them do exactly that.
A spat between manager and players almost saw Karanka walk out but he returned and Boro went unbeaten for the rest of the season, drawing with Brighton and Hove Albion in a final-day promotion shoot-out in a bouncing Riverside Stadium to seal their return behind Burnley in the automatic promotion places.
The lowest point of the season came with the shock passing of local commentator Alastair Brownlee, but fans, players and manager united as one to claim a Premier League spot in his name.
"He will be looking down on us, he's an extra player and will always be supporting us," Karanka said mid-season.
A tribute video to the legendary broadcaster renowned as 'The Voice of the Boro' was played before the final-day clash with Brighton, and chants of 'One Ali Brownlee' are certain to be heard around the Premier League grounds this season.
What to expect from Boro
As a disciple of Jose Mourinho, it is unsurprising that Karanka favours a 4-2-3-1 formation, and has been accused of stubbornness in rarely choosing to deviate from this.
Boro are built from the back - their defensive record last season was the best in England - but their play is not as defensive as some would suggest. In fact, they may fare better in attack in the top flight than in the Championship, as their biggest struggles last season came when teams lower down the table sat back and played to frustrate rather than attack.
With the signing of Alvaro Negredo, Karanka has suggested he could be tempted to play two up front, as he has done on occasion in the past. He has played both 4-4-2 and 3-5-2 on occasion, but these systems are very much second and third choice.
Boro look to the stars in the transfer window
Middlesbrough have made waves around Europe with their transfer window, with a number of formerly world-class players making the move to Teesside.
Victor Valdes had allegedly been speaking to the club for around two years before joining earlier in the summer, while Alvaro Negredo could be one of the signings of the summer if he can rediscover his lethal early form for Manchester City.
Both deals are low-risk: Valdes' contract is only two years long, and Negredo's initial deal is a loan stint with a non-binding option to buy for €10 million.
Marten de Roon looks like a clever signing, too. The Dutch midfielder's tackling and interception stats were among the best in Europe last season, and he will add bite to the side - though likely at the expense of club captain Grant Leadbitter.
Former Ajax starlet Viktor Fischer was touted as one of the brightest prospects in Europe just a couple of years ago but Boro snapped him up for less than £4 million, while the re-signing of former loan star Gaston Ramirez was at the top of many fans' transfer lists at the start of the window.
Antonio Barragan and Bernardo Espinosa will provide competition at the back, while Brad Guzan will hope to battle Valdes for the number one shirt.
However, perhaps their most important piece of business was to tie down defender Dani Ayala to a new deal. The Spaniard has signed a new contract until 2020 to put to bed months of speculation, and is perhaps the most important part of Aitor Karanka's side.
Reasonable pre-season gives glimpse of progress
Summer preparations once again took the Boro squad back to their familiar haunt of Marbella for a week's training and a number of friendlies.
Lower-league clubs such as York City and Doncaster Rovers have been swatted aside, Aston Villa were roundly beaten 3-1 from behind while the only defeat so far has some at the hands of Real Betis.
Ramirez struck the crossbar with a free-kick in a goalless draw away to Udinese, while at time of writing Real Sociedad are the final opponents before the season gets back underway, in the only pre-season encounter to take place at the Riverside.
Striking duo the players to watch
If Karanka does gamble on a two-striker formation, Rhodes and Negredo look as if they could form a potent partnership up top.
Both players have points to prove - Negredo has had a poor couple of years since moving to Valencia, and no Premier League club has ever taken the risk on Championship poacher extraordinaire Rhodes - but both have been in superb form in pre-season, and look to be in the mood for goals.
Metronomic midfielder Adam Clayton is the man who makes the team tick, and he and young centre-half Ben Gibson will be looking at the examples of players such as Danny Drinkwater and hoping to make a case for an England call-up.
Strengths at both ends of the pitch
Keeping things tight at the back is Boro's forte, and clean sheets in the cups at the Etihad and Old Trafford suggest that they have a Premier League defence worthy of the name.
When Ayala and Gibson have played the full 90 minutes together, Boro have lost just one league game in the last two years - a freak 4-3 defeat at Fulham when Boro sent their goalkeeper up for a last-minute corner and conceded as a result.
Ayala's fitness is a concern, and he is likely to miss at least the first game of the season, but if the pair can continue to grow their fearsome partnership with either Valdes or Guzan behind them, Boro will have a solid foundation on which to build.
Stewart Downing met some criticism for his performances in the Championship last season, but his experience in the top flight will be crucial; two years ago, he was one of the division's outstanding creative players at West Ham, and he will be looking to recapture that sort of form.
Perhaps their greatest strength, though, is their never-say-die attidude; last-gasp wins against Hull City, Reading and Bolton Wanderers exemplified this in the run-in last term.
One-paced Boro could lack killer touch
A lack of a real Plan B is an accusation which has been levelled at Karanka in the past, and Boro do struggle to win games in which they fall behind.
Part of the reason for this is a lack of genuine pace in the side, with Albert Adomah and Emilio Nsue's right-wing partnership the only real source of pace in the squad.
With four forwards in Negredo, Rhodes, David Nugent and Cristhian Stuani, Boro have experience up front and a varied skill-set - but pace is not there in abundance. Another attacking midfielder and two defenders are still expected to arrive, but a pacy striker is not thought to be high on Karanka's list of priorities.
Karanka's temperament is also a worry. A man of passion and emotion, he has found that players do not always respond to his honest, fiery ways - Adomah and Downing can vouch for that, while the argument that nearly derailed last season could resurface if things start to go wrong.
Boro will need patience and togetherness if they are to make an impression on the top flight. The last ten games of last season seem to suggest that the latter is there in abundance, but an expectant fanbase could be accused of being lacking in the former.
Teenage defender Fry making the headlines
There is real excitement about attacking pair Harry Chapman and Arnel Jakupovic in the club's youth ranks, but the chances of either of the two being thrown into a fight for Premier League survival are slim.
Chapman was loaned out to Barnsley at the end of last season, and both could find themselves earning their stripes in the Football League.
Defender Dael Fry was thrown in at the deep end as a 17-year-old on the opening day against Preston North End last season, and his Man of the Match performance earned him a number of outings over the rest of the campaign.
As things stand, an injury crisis in defence could lead to Fry seeing some action at the beginning of the Premier League campaign, alongside fellow academy graduate Gibson in the heart of defence.
Gibson himself is only 23 and is an almost certain future captain, while reports in May claimed that he was to be fast-tracked into the England set-up due to a shortage of left-sided defenders.
Young midfielder Julien de Sart has looked tidy in pre-season but is some way down the pecking order, so could also find himself spending some time out on loan.
Predicted finish - 15th
If they can hold things together off the pitch, Boro have enough to stay up, especially with their fellow promoted clubs Burnley and Hull City failing to make an impact on the transfer market.
A 17th-place, goal-difference, final-day survival would be more than enough for Karanka, whose long-term project is right on track. Some good signings and a solid defence should see Boro somewhere around the 15th place mark come the end of the season.
If Negredo or Rhodes can hit the goal trail, there is no reason why they shouldn't be able to aim for a lower mid-table finish, with clubs such as Watford and Bournemouth (not to mention Leicester City) in recent years showing that the promoted clubs are no pushovers.