Boro's week-long stay in Portugal came to a winning conclusion after Chesterfield were beaten on Saturday evening.
Goals from Cristhian Stuani and Patrick Bamford secured Garry Monk a first win as Boro manager as his men eased past the League Two side in Vila Real.
Stuani showed a good nose for goal by delivering a confident strike to put Boro 1-0 up inside the opening 20 minutes as Monk's side dominated proceedings.
The Uruguayan almost added a second when he tried his luck with an effort which went just over the bar.
Boro passed the ball well and kept Chesterfield penned back for long periods, and there were plenty of encouraging signs as the boss again opted to field two different XIs in each half of the game.
Boro started the second half in equally positive fashion and after Gaston Ramirez went close, Adama Traore appeared to have good claims for a penalty waved away.
Shortly before the hour-mark, Traore again forced his way into the box and this time the referee had no doubts after the Boro man appeared to be pulled back. Bamford stepped to convert clinically to double the advantage.
Boro continued to be a threat and Chesterfield had to be alert to keep the score down to 2-0 as Monk's side picked up a first win of the summer.
First-half XI: Dimi, Fabio, Fry, Gibson, Baptiste, Clayton, Leadbitter, Forshaw, Soisalo, Stuani, Gestede.
Second-half XI: Ripley, Christie, Ayala, Mahmutovic, Friend, Howson, De Roon, Ramirez, Traore, Tavernier (Chapman 85), Bamford.