A superb second half fightback earned Boro's Under-21s all three points against Borussia Monchengladbach at the Riverside.
The German side took their opportunities in front of goal in the first half of the Premier League International Cup match, surging into a 2-0 lead despite some bright Boro play.
Mark Tinkler's side kept at it after the break and were rewarded as late goals by Ajay Matthews and Jack Stott looked set to earn them a share of the spoils.
There was still time for Matthews to strike the winner in stoppage time, though, as Boro secured a tremendous victory.
The first half was an entertaining watch as both sides produced plenty of bright moments, but it was the visitors who proved to be the more clinical.
They took the lead on two minutes when Charles Herrmann was played in on goal and produced a cool finish.
Boro goalkeeper Tom Glover kept out a Grant Ranos free-kick before the hosts responded strongly as they gained a foothold in the game and worked the ball into dangerous areas.
Sonny Finch had a shot blocked, Gladbach goalkeeper Maximilian Neutgens kept out a sweet strike by Matthews and George Gitau drilled one narrowly past the post.
Matthews was also just unable to get clean enough contact on a corner to beat Neutgens, who then pulled off a superb fingertip save to stop a Luke Woolston free-kick.
Woolston's set-piece delivery was proving a thorn in Gladbach's side, but Neutgens would not be beaten and the away team took full advantage at the other end.
Against the run of play, substitute Winsley Boteli pounced on a loose ball and slotted past Glover with eight minutes of the first half remaining.
There could have been a third before half-time, but Woolston raced back to the goal-line to clear a strike from Boteli.
Middlesbrough U21: Glover, Gitau, Woolston, Hunt, McCormick, Finch, Cartwright, Stott, Lennon (Nkrumah 56'), Bakre (Simpson 78'), Matthews
Subs: Lindo, Patterson-Powell, Nkrumah, Coulson, Traore, Simpson, Connor
Borussia Mönchengladbach U21: Neutgens, Berko (Worsdorfer 58'), Foss (Najjar 45'), Vali Fard, Ranos, Dasbach (Uwakhonye 21'), Herrmann (Fleck 45'), Sauck (Boteli 35'), Stange, Swider, Fukuda
Subs: Uwakhonye, Najjar, Fleck, Worsdorfer, Trippel, Boteli
Boro created the better opportunities after the break, the first of which went to Hazeem Bakre, who dragged wide from 10 yards.
Finch was denied by a block after being played in by Harley Hunt, who himself went close with a header which Neutgens tipped over.
Boro needed Glover to keep the scoreline at 2-0 as he superbly thwarted visiting captain Veit Stange, while Shio Fakuda later headed off target from close range.
As the game entered the closing stages, Mark Tinkler's side were in need of a goal to force a grandstand finish.
Bakre attempted to find it with a powerful drive which cleared the crossbar, before Matthews did pull one back with 11 minutes remaining, heading a corner into the bottom of the net.
Matthews headed a further opportunity narrowly wide as Boro went in search of a point, and the equaliser deservedly came on 85 minutes.
It was Stott who provided it with a stunning 25 yard drive which arrowed into the corner of Neutgens' goal.
Stott was inches away from winning it with an even better strike which dropped just past the post.
But there was still time for Matthews to prove the match-winner, firing into the roof of the net from an acute angle two minutes into stoppage time to complete the comeback.
