Boro snatched a dramatic late win as Tommy Conways 93rd-minute penalty saw off the challenge of Plymouth Argyle.
The Teessiders took an early lead when Finn Azaz netted from close range against his former club, but the visitors were level by the quarter-hour mark.
Boro pushed and probed against the battling Pilgrims and looked set to be frustrated in their efforts until second half stoppage time.
Conway won and scored from the spot to spark jubilant scenes at the Riverside and secure maximum points.
Possession
24%Shots
16Shots On Target
5Corners
1Fouls
100
0
Cards
2
1
There was one change to the Boro team which started the previous week’s game at Millwall, with Marcus Forss replacing Delano Burgzorg in the XI.
It took 12 minutes for Azaz to put Michael Carrick’s men in front.
Anfernee Dijksteel’s through ball found Tommy Conway on the inside-right channel and when his dinked effort came back off the post, Azaz was there to finish from close range.
Conway had a header saved shortly afterwards but Argyle quickly drew level, with Mustapha Bundu winning the ball high up the pitch before firing home first-time.
There were chances at both ends across the remainder of the first half, although Boro were dominant in possession.
Azaz fired over from the left, Aidan Morris had a header saved and Marcus Forss was denied by a block as we attempted to restore our advantage.
The Pilgrims were dangerous at the other end, with Mark Travers needing to be alert to keep out strikes from Darko Gyabi and Ryan Hardie, who had been played through on goal by a ball over the top.
Whittaker had a shot deflected wide on the stroke of half-time but the sides went in level.
Middlesbrough: Travers, Dijksteel (Fry 61'), Howson, van den Berg, Iling-Junior (Giles 89'), Morris, Hackney, Forss (Iheanacho 73'), Whittaker (Burgzorg 89'), Azaz, Conway
Subs: Barlaser, Fry, Iheanacho, Burgzorg, Glover, Edmundson, Giles, Palmer, Anton Palmer
Plymouth: Hazard, Edwards, Szucs, Pálsson, Pleguezuelo (Puchacz 88'), Mumba, Gyabi (Callum Wright 72'), Randell, Houghton (Boateng 89'), Hardie (Obafemi 89'), Bundu (Tijani 78')
Subs: Ogbeta, Callum Wright, Obafemi, Puchacz, Boateng, Tijani, Baidoo, Grimshaw, Issaka
Whittaker was again the first to have a sight of goal in the second half, cutting inside from the right before unleashing a fierce drive which Conor Hazard did well to punch away.
Sam Iling-Junior had a free-kick deflected over while at the other end, Boro breathed a sigh of relief when Ryan Hardie blazed a 12-yard opening.
The same player later drew a block from Rav van den Berg while Boro were largely reduced to strikes from distance, several of which were charged down.
That changed when Conway was played in down the left of the area, but he was prevented from putting us back in front by a tremendous one-handed save from Hazard, before later heading wide from a Whittaker cross.
Whittaker was denied a penalty after going down under a sliding challenge in the area, and another strong shout for handball was later waved away.
The Boro frustration findally ended in the second minute of stoppage time when Joe Edwards fouled Conway in the area and received a straight red card.
Conway made no mistake from the spot to deliver what could prove to be a vital three points.