Meanwhile, the home side, who are now in the National League, will be participating in their first fixture of the summer.
Match preview
On the back of missing out in the Championship playoffs, Michael Carrick faces a difficult job to rouse a club that at one stage looked the most likely to earn promotion to the Premier League.
Carrick has reacted by trying to ensuring that there are plenty of fresh faces in his Middlesbrough squad with familiar and not so familiar names arriving at the Riverside Stadium.
Queens Park Rangers goalkeeper Seny Dieng and Manchester City youngster Morgan Rogers will be known by many Boro fans, while Netherlands Under-20 international Rav van den Berg will be less so.
Nevertheless, when Premier League loan additions inevitably arrive at some stage, Carrick will have one of the strongest squads in the division at his disposal, and expectations are far greater than they were in 2022-23.
Middlesbrough got their pre-season campaign underway by defeating Vitoria de Guimaraes in a behind-closed-doors friendly on July 8, Marcus Forss scoring the only goal of the game.
Hartlepool United have taken a different approach to pre-season so far, the newcomers to the National League still yet to play their first encounter of the summer.
Nevertheless, manager John Askey has been busy in the transfer market, a wave of talent arriving from the EFL and non-league to give his squad all the makings of being difficult to stop this campaign.
Bolton Wanderers goalkeeper Joel Dixon and Mansfield Town left-back Kieran Wallace appear to be the standout names, the latter in particular having earned regular League Two action over the past 18 months.
After relegation from that division, Hartlepool face five friendlies, starting with Boro and ending with a home encounter against another North-East giant in Sunderland.
Middlesbrough friendly form:
W
Team News
Boro opted against publishing a teamsheet for their friendly in Portugal, leaving an air of uncertainty regarding this match.
However, it was revealed that Van den Berg and fellow new signings Alex Gilbert and Sammy Silvera all made their debuts.
Dieng may feature between the sticks for this contest after his recent arrival, but Boro's squad will be split over two games that are being played within 24 hours of each other.
Meanwhile, Askey will want to provide as many players as possible with sufficient minutes ahead of their trip to Scotland.
The incoming Peter Jameson, Kieran Burton, Matty Dolan, Emmanuel Dieseruvwe and Chris Wreh will all hope to be handed some game time.
We say: Hartlepool United 1-4 Middlesbrough
Having defeated Portuguese opposition, this certainly represents a different kind of test for Boro at this stage of their schedule. Nevertheless, the extra game time in their legs should only benefit them and we expect a routine victory to be posted on Friday.