Middlesbrough never recovered from conceding a couple of quick-fire first-half goals despite leaders Wolverhampton Wanderers later being reduced to nine-men at the Riverside.
Helder Costa volleyed the visitors in front shortly after the half-hour mark before Ivan Cavaleiro doubled their tally just five minutes later.
However, both Ruben Neves (56) and Matt Doherty (71) were dismissed following the interval, although it took until added time for Patrick Bamford to discover a reply.
Neves earlier had Boro goalkeeper Darren Randolph at full-stretch before Barry Douglas delivered to the far post for Costa to strike, only moments after his first effort was denied.
Republic of Ireland international Randolph soon kept out Willy Boly’s header, but once again Cavaleiro took advantage of the rebound to extend the lead up to the break.
After last-man George Friend had already survived dismissal claims, the hosts were offered a way back as Neves received a couple of yellow cards just minutes apart.
And their hopes were suddenly increased with Doherty also sent-off for similarly collecting his second caution of the evening.
Boro had around twenty minutes to save themselves; substitute Jonny Howson struck wide before John Ruddy turned aside from Adama Traore and Stewart Downing curled behind.
But it took until the closing moments for Bamford to take advantage of Traore’s flick and reduce the deficit; that ahead of Downing shooting narrowly wide as time and hope finally ran out.
Middlesbrough: Randolph, Shotton (Cranie 70), Ayala, Gibson, Friend, Clayton (Assombalonga 70), Leadbitter (Howson 63), Besic, Traore, Bamford, Downing
subs (unused): Konstantopoulos, Fry, Harrison, Baker
Goals: Bamford (90)
Wolverhampton Wanderers: Ruddy, Bennett, Coady, Boly, Doherty, Neves, Saiss, Douglas, Cavaleiro (N’Diaye 58), Afobe (Bonatini 63), Costa (Gibbs-White 84)
subs (unused): Batth, Vinagre, Hause, Norris
Goals: Costa (32), Cavaleiro (37)
Ref: S. Attwell
Att: 27,658
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