Michael Rose stunned Pompey as nine-man Coventry rescued a point with a 3-3 draw on a night of Fratton drama.
Rose’s finish with four minutes left meant the Blues somehow threw away a maximum return in front of a crowd of 18,748, with the boos ringing out at full-time.
It proved a breathless night under the Fratton lights as Pompey goals from Ronan Curtis, John Marquis and Gareth Evans flew in.
Jordy Hiwula put the side in front after just three minutes before Matt Godden’s penalty with 15 minutes left made for a nervy finale.
And then with four minutes remaining - and despite having both Fankaty Dabo and Gervane Kastaneer sent off - Mark Robins’s side salvaged a draw as a long throw wasn’t dealt with and Rose did the rest from 10 yards.
It was a sickening blow and there will be strong questions asked by the Fratton faithful quite how their side managed to shoot themselves in the foot.
Pompey made three changes as Ross McCrorie, Evans and Sean Raggett came in for Andy Cannon, Christian Burgess and Anton Walkes.
It was a frenetic first 45 minutes with both defences looking like they could be regularly breached.
That was underlined by the terrible defending for Coventry’s opener as the yellow away shirts countered and streaked clear, with summer Pompey target Matt Godden in acres and picking out Jordy Hiwula who emphatically dispatched the finish from 12 yards.
The home side were level seven minutes later with the constantly dangerous Marcus Harness providing the sumptuous ammunition for Curtis to head from a few yards out.
Pompey should’ve had a penalty four minutes later when Marquis burst into the box and was caught by Michael Rose on the byline, but ref Kevin Johnson bemusingly chose to play on.
The home side were forced into a change 13 minutes before the break when Lee Brown limped off for Brandon Haunstrup.
And the Waterlooville lad played a big part in his side’s second goal three minutes before the break.
A Hollywood crossfield ball from the again excellent Tom Naylor found Curtis, who back-heeled to Haunstrup and it was his centre which allowed Marquis to open his Pompey account with a tap in.
Pompey were indebted to Craig MacGillivray once again as he produced a fine stop to his right to deny Godden six minutes after the restart, after Downing was caught out by a ball over the top.
And that save was looking even sweeter when Evans made it 3-1 five minutes later as he caught Kyle McFadzean in possession and advanced before finishing with aplomb from just inside the box.
Coventry were down to 10 men two minutes later as Dabo was dismissed for a second yellow card after a deliberate handball.
There was a lifeline for the visitors with 15 minutes left as Close caught Liam Kelly in the box and Godden sent MacGillivray the wrong way.
Then Coventry were down to nine as sub Gervane Kastaneer took out Downing and got a second yellow.
The Sky Blues had the ball in the net with eight minutes left but the flag was up after Kelly finished from inside the six-yard box.
But that warning wasn't heeded as Rose struck to make it a grim night as boos rang around Fratton on the full-time whistle.