A stunning comeback saw North End make it six straight away wins with their first win on Teesside in the league since 1972.
Ashley Fletcher had given Tony Pulis’ side the lead in the first half at the Riverside Stadium, but after Daniel Ayala saw red for challenge on Brandon Barker who was through on goal, Paul Gallagher converted the resulting free kick for his 100th career goal and then Jayden Stockley headed home the winner on a famous night in Middlesbrough.
Manager Alex Neil made two changes to the side, with Ben Pearson returning at the heart of the midfield and Josh Earl coming in to a re-jigged backline for the suspended Darnell Fisher, the No.3 playing left-wing back, Alan Browne playing on the right side, with a back three in front of Declan Rudd.
The hosts started the game brightly and Jonny Howson on six minutes had a shot from 25 yards out, that Declan Rudd had to be alert to palm behind. From the resulting corner by Mo Besic, the ball was flicked on by Fletcher and Daniel Ayala hit the outside of the back post from close range.
The woodwork was struck again shortly after as Jon Obi Mikel found space to for an effort from 20 yards out that came off the foot of the left-hand upright, deflecting off Jordan Storey and eventually cleared by Earl.
Mid-way through the half the Lilywhites suffered a blow as Browne was forced off with what appeared to be a left ankle injury, Joe Rafferty coming on to replace him.
The opener came just after the half hour mark as Besic again charged forward and fed the ball out to the left of the penalty area where Fletcher found space to shoot, the ball flicking up off Storey, giving Rudd no chance as it floated into the right-hand corner of the goal.
The North End manager made an immediate change, reverting to four at the back and the remaining minutes of the half saw the visitors gain the ascendency, dominating the possession, and in the second of three added minutes, Rudd was needed again, making a fine save at the feet of Britt Assombalonga after a flick around the corner by Fletcher.
At the interval another change saw Brandon Barker introduced, Earl replaced, with the on loan Manchester City man joining fellow loanee Lukas Nmecha and Sean Maguire in a now three-man attack.
But on 61 minutes a big moment in the game came as Ayala was given a red card by referee Keith Stroud after a two-footed challenge on Barker on the edge of the Boro penalty area. It was right on the edge of the box ten yards in from the left corner.
And from the resulting free kick the green-clad side were level. Gallagher lined it up and played it to Hughes, who stood the ball dead for the North End skipper to curl the shot into the bottom right hand corner, giving Randolph no chance, his 100th career goal.
Ben Pearson was next to test Randolph with a shot from the edge of the ‘D’ coming off substitute Dael Fry and ricocheting up into the hands of the grateful Republic of Ireland international custodian.
Another hugely controversial moment came with 11 minutes left as Nmecha had beaten George Friend all ends up, only to be brought down in the right edge of the penalty area, but this time the referee gave nothing, when a penalty seemed the only decision!
But the second came on 81 minutes and it was another substitute. Andrew Hughes picked up the ball 25 yards out after some PNE pressure and hit a shot that came off Howson, but Stockley was alert and headed home powerfully from close range.
Two great chances came to Nmecha after the goal, Randolph denying him with some superb goalkeeping on both occasions, after the No.45 used his pace down the right to get away from Friend and force stops from the keeper.
Middlesbrough line-up: Randolph, Mikel (Tavernier, 85), Friend (c), Ayala, Shotton, Assombalonga, Howson, Fletcher (Fry, 64), Flint, Wing, Besic (Hugill, 77). Subs not used: Konstontopoulos, Clayton, Downing, Saville.
PNE line-up: Rudd, Earl (Barker, 46), Hughes, Pearson, Storey, Davies, Nmecha, Johnson, Maguire, Browne (Rafferty, 22), Gallagher (c) (Stockley, 75). Subs not used: Crowe, Ginnelly, Ledson, Huntington.
Attendance: 21,088 (376 PNE fans)
Referee: Mr K Stroud