Blues lose penalty shoot out.
Curtis Main bagged a brace as Pompey fought from two goals down to draw with Reading U23s in the Checkatrade Trophy.
But it was the visitors who claimed a bonus point by winning a marathon penalty shoot-out, despite the heroics of goalkeeper Liam O’Brien.
Andrija Novakovich’s early finish and a Joseph Mendes penalty looked to have secured victory for the visitors.
But Main struck twice – the second of which was a fine first time finish – to haul the Blues level at a sparsely-populated Fratton Park.
The match attracted a crowd of just 1,355 – comfortably Pompey’s lowest post-war attendance for a competitive home fixture.
Paul Cook rung the changes for their second group stage fixture, with Matt Clarke the only player to keep his place from Saturday’s league defeat to Doncaster.
But they got off to a poor start, with the visitors breaking the deadlock after just six minutes.
Mendes showed blistering pace to latch onto Liam Kelly’s pass and coolly laid the ball back for Novakovich to slot home.
Most of the first half action then took place at the other end of the pitch, although the Blues never really tested keeper Anssi Jaakkola.
Thomas McIntyre did well to nip in and intercept a threaded pass from skipper Kyle Bennet before it could reach Michael Smith.
The two Blues players combined well again moments later, but after swapping neat passes the striker scuffed his shot wide.
Bennett then teed-up Adam Buxton down the right and the full-back’s cross had to be diverted behind by Danzell Gravenberch with Main waiting to pounce.
Pompey’s best chance of the half fell to Milan Lalkovic on 23 minutes, with his goal-bound effort just about scrambled to safety.
The Royals did threaten at the other end moments later, but O’Brien was able to gather Dominic Samuel’s fierce low drive at the other end.
And Ben Close hit a similarly powerful shot of his own, only for the ball to narrowly clear the crossbar.
But the Blues were dealt a blow just before the break when Buxton went down following a 50/50 challenge and had to be replaced by Gareth Evans.
Reading U23 1
Pompey had a chance to level moments after the restart, but Jaakkola was wise to Evans’ neat flick after Bennett had sent a corner towards the near post.
Instead, they found themselves further behind when referee Oli Langford spotted an Amine Linganzi handball in the box.
Mendes stepped up to take the spot-kick and smashed the ball high into the net, giving O’Brien – who guessed the right way – no chance.
It did not take long for the hosts to reduce their deficit, however, as MAIN slid in to squeeze Evans’ cross past Jaakkola.
And it was MAIN who drew the Blues level just past the hour mark, converting Bennett’s pass with a fine first time finish into the bottom corner.
The striker was denied the chance to complete his hat-trick, though, as he was soon withdrawn for Kal Naismith.
Reading still had chances of their own as the game entered its closing stages and O’Brien got down well to save Novakovich’s deflected effort.
It was Pompey looking the more threatening, however, and Smith was inches away from meeting Naismith’s teasing cross.
Jaakkola then failed to hold substitute Adam May’s thumping strike and was relieved to see the ball land safe.
And it took a vital last-gasp challenge from Gravenberch to prevent Smith from being sent clear by Bennett’s incisive pass.
But the Royals wasted a glorious opportunity to snatch a stoppage-time winner when an unmarked Tyler Frost fired straight at O’Brien from just a few yards out.
That meant a penalty shoot-out would be held to see which team walked away with an additional point.
Smith, Naismith and Evans all scored, but Jaakkola denied both Bennett and Lalkovic and it looked like that was that.
O’Brien made a couple of stops of his own to take it to sudden death, however – and made another fine save to keep out Tennai Watson’s effort.
But May and Jack Whatmough both failed to beat Jaakkola, allowing Frost the chance to secure Reading an additional point.
Pompey (4-4-2): O’Brien; Buxton (Evans 44), Whatmough, Clarke, Haunstrup; Bennett (c), Linganzi, Close (May 73), Lalkovic; Smith, Main (Naismith 69)
Goals: Main 57, 63
Subs not used: Hall, T.Davies, Oxlade-Chamberlain
Reading U23 (4-4-2): Jaakkola (c); Watson, Gravenberch, McIntyre (Griffin 18), Blackett; Rinomhota, Frost, Kelly, Samuel; Novakovic (Richards 78), Mendes
Goals: Novakovic 6, Mendes 52 (pen)
Subs not used: Moore, Vancooten, East, Bennett, Cardwell
Referee: Oli Langford
Attendance: 1,355 (133 away fans)