A controversial late penalty from David Bremang denied Pompey victory at Crawley in their opening Papa John’s Trophy group stage contest.
The visitors had earlier turned the game around, with Clark Robertson and substitute Dane Scarlett on target after Dom Telford had also struck from the spot.
But the Blues were also denied a bonus point after being beaten 6-5 in the resulting penalty shoot-out.
Danny Cowley made 10 changes from the side that beat Port Vale in the league at the weekend, with Ronan Curtis the only player to keep his spot.
There was a debut for Josh Oluwayemi between the sticks, while Denver Hume made a first appearance in more than five months after recovering from a back problem.
Robertson skippered the side, with Haji Mnoga and a fit-again Zak Swanson completing the back-line.
Reeco Hackett, Joe Morrell, Jay Mingi and Michael Jacobs were in midfield, while Curtis was partnered by Joe Pigott up front.
Academy scholars Malachi Osei-Owusu, Harvey Laidlaw and Adam Payce were all included among the substitutes.
The visitors looked to make a fast start and a couple of fortunate ricochets provided chances in the opening stages.
Hackett was the recipient of the first, but his effort was diverted behind, while a later Curtis attempt flew straight at David Robson.
Instead it was the hosts who broke the deadlock on eight minutes after James Tilley went down in the box under Pigott’s challenge.
Referee Sam Allison decided it was a foul by the Pompey striker and Telford stepped up to score from the spot.
Pompey dominated possession and territory as the first half progressed, but their moves broke down in the final third.
Their best chance came when Hackett dug out a shot from outside the area that Robson did well to turn around the post.
Pigott then felt he should have been awarded a penalty when he tried to lift the ball over Tony Craig and the ball struck the defender’s arm, but Allison waved play on.
And Crawley might have extended their advantage before the break, with Telford firing wide from just a few yards out following good work from Tilley.
Tilley then flashed a dangerous ball across the face of goal and a stretching David Bremang could only turn it into the side netting.
Half Time: Crawley 1 Pompey 0
Cowley made a couple of changes at the break, with Morrell and Hume withdrawn for Tom Lowery and Kieron Freeman.
It failed to immediately spark the visitors into life and they still struggled to break down an organised Crawley defence.
Despite that, the large congregation of Blues fans behind the goal – and to one side – remained in fine voice.
Another double switch followed just past the hour mark, as Jacobs and Curtis made way for Owen Dale and Scarlett.
The latter thought he should have been awarded a penalty after tangling with Travis Johnson, but Allison again disagreed.
A spell of persistent Pompey pressure then ended with Dale having a shot deflected over, while Robertson could not guide his header on target from the resulting corner.
But it was a better effort from the skipper moments later, with ROBERTSON rising highest to plant the ball into the net from Lowery’s delivery.
Teenage midfielder Payce was then given his second appearance in this competition, coming on for Swanson.
And it was another youngster celebrating moments later, with SCARLETT collecting Mnoga’s pass, spinning around Craig and drilling a shot into the bottom corner.
The visitors continued to threaten as the seconds ticked down, but it was Crawley who snatched a draw in stoppage-time.
Tilley went down in the box under Lowery’s soft challenge and Pompey were furious with the decision to award a penalty, which Bremang slammed into the roof of the net.
It meant that penalties would be required to see who claimed a bonus point and Scarlett sent the first one wide.
But Hackett, Dale, Lowery, Pigott and Robertson all confidently found the target and Oluwayemi denied Tilley.
Freeman’s effort was kept out by Robson, however, meaning Raf Khaleel could step up to ensure Crawley would take two points from the game.
Crawley (3-4-1-2): Robson; Johnson, Ransom, Craig; Al-Hussaini (Adebowale 75), Jenks (Powell 52), Wells (Khaleel 75), Marshall (Ogungbo 66); Tilley; Telford (c) (Nadesan 75), Bremang
Goals: Telford 8 (pen), Bremang 90+5 (pen)
Booked: Wells
Subs not used: Addai, Shubbar
Pompey (4-4-2): Oluwayemi; Swanson (Payce 77), Mnoga, Robertson (c), Hume (Freeman 46); Hackett, Morrell (Lowery 46), Mingi, Jacobs (Dale 62); Curtis (Scarlett 62), Pigott
Goals: Robertson 74, Scarlett 81
Booked: Jacobs, Hackett
Subs not used: Osei-Owusu, Laidlaw
Referee: Sam Allison
Attendance: 2,314 (1,111 Pompey fans)