Pompey lost 4-3 to Reading under-23s on penalties in the Checkatrade Trophy at Fratton Park tonight.
That’s after it finished 2-2 after 90 minutes with Curtis Main grabbing himself two goals - earning Paul Cook’s side a point.
Liam O’Brien saved three spot-kicks but misses from Kyle Bennett, Jack Whatmough, Adam May and Milan Lalkovic meant the Royals were given an additional point.
The game will be remembered for Pompey’s lowest post-war attendance turning out for the tie in the much-maligned competition.
A crowd of 1,355 were at the game but the defeat means the Blues remain in it still with Bristol Rovers to play in the final southern group A game.
The first chance saw Michael Smith glance a header just wide from Buxton’s cross.
But Pompey fell behind after six minutes as Joseph Mendes beat Liam O’Brien to a through ball and squared for Novakovich to finish from five yards.
The response saw Michael Smith scuff a shot wide from 20 yards before Milan Lalkovic forced a save out of Annsi Jaakkola from Kyle Bennett’s corner.
Ben Close then thumped a 25 yarder just over the top in the 33rd minute.
Smith was inches away with a curler from the apex of the box as Pompey pushed for a leveller.
The half finished with concern, however, as Buxton came off worse from a 50-50 tackle and was replaced by Gareth Evans.
It got worse for Pompey seven minutes after the restart as Reading increased their lead from the spot.
It appeared Amine Linganzi was the man penalised for a handball which allowed Mendes to thump a convincing effort past O’Brien.
But the Blues were back in it five minutes later as Evans provided the ammunition for Main to slide in and finish at the back stick.
And six minutes later Main had his second with a cool finish from 12 yards from Bennett’s pass.
Evans then fired just over the top from 25 yards as Pompey continued to have the better of it.
But there were to be no further goals meaning each team picked up a point and the game went to penalties.
O’Brien made his mark with a series of stops but it was Frost who fired the winning kick in the shootout - to pick up the extra point on offer.