The Blues dug in with a gutsy defensive performance in an attempt to preserve a 2-1 advantage given to them through Christian Saydee’s two first-half goals.
It was real backs to the wall stuff from John Mousinho’s men, who had to fight off wave after wave of Middlesbrough attacks, particularly after the break.
However, Owen Moxon’s foul on Isaiah Jones earned the hosts a 90th minute penalty, converted by substitute Tommy Conway, to secure a 2-2 draw.
Just like their previous away trip at Leeds, Pompey were foiled victory at the death – and here are our player ratings...
5. Connor Ogilvie - 7
Great first-half moment when he thundered into successive tackles in front of the South Stand and won them both. Strong in the air and kept Doak quiet, with the winger even getting a booking for fouling him. Photo: Jason Brown
6. Issac Hayden - 7
(Replaced on 69 mins by Andre Dozzell) Handed his Pompey full debut and showed the tenacious side to his game on the stroke of half-time, although escaped a booking for the challenge. Very solid first outing. Encouraging. Photo: Jason Brown
7. Freddie Potts - 7
Bounced back from tough time at Blackburn and what a wonderful pass to pick out Ritchie to make it 1-1. Still learning, prone to the odd misjudgement what some talent. Photo: Jason Brown
8. Matt Ritchie - 9 - MOM
Back in the team in place of injured Paddy Lane - and what a return. Lovely run and classy finish with an angled left-footed shot to level for 1-1. Then grabbed winner eight minutes from time with his right foot. Had never scored at Fratton Park for Pompey before. Special moments for one of Pompey's own. Photo: Jason Brown