Boro tasted defeat as Bristol City came from behind at Ashton Gate.
Tommy Conway's header gave us the lead in a first half in which Boro had to show plenty of resilience at the back.
But two second half finishes from George Earthy turned the game around and handed the Robins maximum points.
Possession
38%Shots
11Shots On Target
4Corners
1Fouls
110
0
Cards
2
0
There were three changes to the Boro team, with Dael Fry, Delano Burgzorg and Anfernee Dijksteel all handed starts.
The early stages saw Michael Carrick’s men control possession, although the hosts went the closest to opening the scoring when Scott Twine’s sweet hit from long range narrowly cleared the crossbar.
Neto Borges and Burgzorg both had sights of goal before Bristol City began to put their visitors under pressure.
Anis Mehmeti dragged wide from the left of the area, Jason Knight curled one past the post and Sinclair Armstrong crashed a shot onto the roof of the net from distance.
Boro showed character to get through a difficult period unscathed and could have took the lead themselves when Morgan Whittaker had a strike blocked and Burgzorg miscued wide from close range.
We did strike the first blow eight minutes before half-time, with Conway taking centre stage against his former club.
Kelechi Iheanacho broke into space in the inside-right channel and when his effort was parried by Max O’Leary, Conway was on hand to head in and silence the home support.
Boro were indebted to Mark Travers for remaining ahead at half-time, though, with the on-loan goalkeeper denying Bird from point-blank range before Mehmeti hooked the rebound wide.
Bristol C: O'Leary, Tanner, Dickie, Vyner, Sykes (Hirakawa 63'), Bird, Knight, Roberts (Pring 63'), Twine, Armstrong (Wells 69'), Mehmeti (Earthy 63')
Subs: Pring, Hirakawa, Williams, Bell, Wells, Bajic, Cornick, McGuane, Earthy
Middlesbrough: Travers, Dijksteel, Fry, van den Berg, Neto Borges, Whittaker (Forss 88'), Morris, Hackney, Burgzorg, Iheanacho (Azaz 83'), Conway
Subs: Barlaser, Ayling, Azaz, Forss, Glover, Edmundson, Iling-Junior, Greenup, McCabe
The home side created a number of opportunities in the second half, with Rav van den Berg doing well to stop the first of them as he blocked from Twine.
Travers saved with his legs from Armstrong and Yu Hirakawa headed over before Bristol City equalised on 72 minutes, substitute Earthy prodding in from the six-yard box.
Twine was denied by a superb Travers stop before he played a major role in what proved to be the winner.
His free-kick crashed against the crossbar and bounced to the feet of Earthy, who made no mistake from close range.
Boro battled in vain for a leveller in what remained of the game as Bristol City saw things out for all three points.
