Much of it was defined by a profound struggle to re-join the loan stars who propelled them to the Championship play-offs the previous season, with Ryan Giles, Cameron Archer, and Aaron Ramsey all joining newly-promoted trio Luton Town, Sheffield United, and Burnley rather than returning to the Riverside Stadium for a second season.
They were no doubt burned by the departure of Chuba Akpom too, who had long been at the centre of a contractual showdown after his 28-goal haul had earned no shortage of suitors, and his clear lack of interest in renewing terms saw an eight-figure transfer to Dutch giants Ajax sanctioned.
Despite all of that, boss Michael Carrick brought in plenty of fresh faces too, one of which being Sam Greenwood on loan from second-tier rivals Leeds United.
Greenwood arrived as one of only two loan transfers across the entirety of the summer and the terms of that deal have been revealed in a fresh update from The Athletic.
Can Middlesbrough sign Leeds United midfielder Sam Greenwood?
Attempting to broker permanent deals for loan players after their temporary spell concludes is often a popular port of call for the clubs in question, and Boro are able to exercise that option if they wish.
The report states that Middlesbrough have a £1.5m option to buy Greenwood at the end of his deal should they be satisfied with his performances, of course.
Both Boro and the player will be running the rule over making the move a permanent one across the rest of the season.
How has Sam Greenwood of Leeds United performed for Middlesbrough?
The versatile attacker has forced his way into Carrick’s plans as of late, starting each of the last two matches – his first two starts for the club – as Middlesbrough have begun to ascend the league table after a sluggish start to proceedings.
Indeed, Greenwood himself had faced some initial teething problems in that stage and failed to register too much of an impact when being introduced from the bench.
However, he was impressive in Boro’s midweek win over Cardiff City and was even more important in their 4-0 Tees-Wear Derby victory against Sunderland, scoring just shy of the hour mark.
