A first Pompey goal for Lee Brown was not enough to beat Peterborough and earn a seventh successive victory.
But the Blues were at least able to extend their unbeaten run into double figures, with a 2-2 draw at Fratton Park.
Brown’s free-kick got the hosts level after Ivan Toney had netted an early opener and Ellis Harrison gave them the lead after the restart.
Mo Eisa hit back for free-scoring Posh, however, to ensure the spoils were shared in an absorbing clash.
Kenny Jackett made two changes from the side that narrowly beat Altrincham in the FA Cup the previous week.
Tom Naylor recovered from a hamstring problem to skipper the team, with Ryan Williams also starting, as Anton Walkes and Marcus Harness made way.
There were a couple of familiar faces in the opposition line-up, with former Fratton full-backs Dan Butler and Nathan Thompson both starting.
It was a laboured start from the hosts at a surprisingly flat Fratton Park, with too many passes going astray.
And – after Alex Woodyard has been booked for fouling Ronan Curtis – Peterborough went ahead through the first decent chance of the contest.
Butler swing in a cross from the left and Oli Hawkins missed his attempted clearance, allowing an unmarked Toney to convert at the far post.
There were soon weak appeals for a penalty at the other end, with Charles Breakspear not convinced that Frankie Kent had fouled Curtis.
Pompey gradually began to grow into the game, although Williams’ deflected drive lacked enough power to test Christy Pym.
An equaliser did finally arrive on 26 minutes, however, with the goal coming from a pretty unlikely source.
Williams was brought down by Louis Reed on the edge of the box and BROWN drilled the free-kick through the wall and past an unsighted Pym.
It ensured the left-back was at last able to celebrate opening his Blues account – on his 68th appearance – racing away before performing a forward roll.
Posh came close to restoring their lead moments later, though, with Kent’s effort kept out by Craig MacGillivray from point-blank range.
It was proving to be an even encounter and Thompson was playing the role of pantomime villain, drawing plenty of boos following a foul on John Marquis.
Pompey were next to go close on 36 minutes when Curtis’ cross was only partially cleared and Pym had to get down to his right to keep out Williams’ effort.
Then, at the other end, Brown did well to put off Thompson, who was only able to prod the ball straight at MacGillivray.
Peterborough United 1
Pompey had an opportunity to take the lead seconds after the restart when Brandon Haunstrup slipped a pass through to Marquis, who scuffed his effort.
Williams then skipped past a challenge on the right and when his cross was not fully headed away, Harrison was unable to bring the ball down to get a shot away.
But HARRISON soon got his name on the scoresheet, collecting a pass from Marquis and firing in an effort that Pym got his hand to, sending the ball trickling slowly over the line.
The visitors tried to hit back and Toney fired one shot over, while another from Thompson was smothered by MacGillivray.
Thompson had perhaps been fortunate not to get booked for a couple of previous indiscretions, but finally saw yellow for illegally halting Harrison’s break.
Peterborough were celebrating a leveller on 72 minutes, however, as Eisa was left in far too much space to convert another Butler delivery.
Jackett responded immediately by making a substitution, with Williams making way for Harness in the forward line.
It was Curtis who soon had a chance to restore Pompey’s lead, though, heading Haunstrup’s corner wide at the far post.
Both sides were looking to get forward in the closing stages in an attempt to turn one point into three.
Haunstrup lifted a neat pass into the box and Harrison did well to evade Thompson’s attentions and get a foot on the ball, only for Pym to make a key block.
The left-footed right-back was forced from the pitch in stoppage-time, though, appearing to injure his foot and having to be replaced by Ross McCrorie.
And neither side were able to find a winner in the extra minutes added on, despite plenty of frenetic play as the seconds ticked down.
Pompey (4-2-3-1): MacGillivray; Haunstrup (McCrorie 90+3), Hawkins, Burgess, Brown; Naylor (c), Close; Williams (Harness 73), Marquis, Curtis, Harrison
Goals: Brown 26, Harrison 52
Booked: Burgess, Brown, Harrison
Subs not used: Bass, Downing, Walkes, Evans, Pitman
Peterborough (3-4-1-2): Pym; Mason (Tasdemir 62), Beevers (c), Kent; Thompson, Woodyard, Reed, Butler; Kanu; Toney, Eisa (Jones 90)
Goals: Toney 10, Eisa 72
Booked: Woodyard, Eisa, Thompson
Subs not used: Chapman, Cartwright, Bennett, Barker, Burrows
Referee: Charles Breakspear
Attendance: 17,643 (531 away fans)
In the greater scheme of things it maybe a minor trophy but seeing you team at Wembley and lifting a trophy is never something to be taken lightly.
The added benefit of also taking away the one trophy Southampton had won that we hadn’t!
Transport was a nightmare, trains absolutely rammed full so Colin drove us to Horsham to try and get a train with some room on it which was a success.
Poor first half with Sunderland deserved leaders but what a turn around second half with the introduction of Gareth Evans and Oliver Hawkins. We thought we had won it with Jamal Lowe’s late extra time goal but as we have seen so many times we cannot defend or kill off the last few minutes of a game and so we faced the trauma of penalties and all five takers hit the spot.
Well done Portsmouth
Checkatrade Trophy – Final
Pompey won the Checkatrade Trophy on penalties following a 2-2 draw with Sunderland at a packed Wembley Stadium.
They were poor in the first half and an Aiden McGeady free-kick meant the Black Cats deservedly led at the interval.
But the Blues were rejuvenated following the restart and Nathan Thompson levelled to ensure an additional 30 minutes.
Jamal Lowe then struck to seemingly secure the win, only for McGeady to scramble the ball home at the death.
That meant a dreaded shoot-out, but Pompey scored all of their spot-kicks, meaning that Craig MacGillivray’s save from Lee Cattermole allowed Oli Hawkins to fire home the winner.
Kenny Jackett made one change from the side that won at Shrewsbury in the league the previous week.
Ronan Curtis was fit enough to start after recovering from severing his finger, meaning that Gareth Evans dropped to the bench.
The teams emerged to a vociferous atmosphere created by a packed crowd at the national stadium.
Pompey’s contingent were whipped up by rousing pre-match speeches from former Fratton heroes David Norris and Hermann Hreidarsson.
But it was the Black Cats who made the brighter start, with Thompson forced to clear George Honeyman’s teasing cross behind.
Lee Brown then made a great challenge right in the corner to stop Lewis Morgan’s charge, as the side from the north-east looked threatening.
Lowe tried his best to cause problems at the other end, although a ball into the box flew straight into Jon McLaughlin’s grasp.
Sunderland were looking more likely to open the scoring and Matt Clarke threw himself in the path of McGeady’s strike.
Pompey’s best opportunity came when Omar Bogle was felled on the right and Brown swung the ball into the mixer.
Christian Burgess rose at the back post, but could not get enough power on his header to trouble McLaughlin.
An effort from Morgan was deflected behind by Brown, while a key Clarke challenge halted Will Grigg’s charge.
There was a rare shot for Pompey on 22 minutes, although Curtis’ effort was always swerving wide of the post.
Then, after Tom Naylor had conceded a free-kick, the midfielder had to nod behind Grant Leadbitter’s delivery.
Sunderland came close to breaking the deadlock soon after when the ball was only cleared as far as Morgan outside the box.
The winger hit a fierce volley that flew through a sea of bodies, but MacGillivray got down well to push the ball clear.
It was only a brief respite for the Blues, however, and they were undone after Thompson had conceded a foul.
McGeady was brought down and picked himself up to curl the ball home, albeit with the help of a deflection off Clarke’s shoulder.
Pompey tried to hit back after the break and when Bogle met a corner from Brown, his header was cleared from the line.
It would not have counted, though, as referee Dean Whitestone had spotted a foul on Luke O’Nien in the build-up.
The Blues were looking a lot brighter and trying to use Lowe as an outlet, but were still lacking a final ball.
Jackett tried to shake things up on 56 minutes, with Curtis being brought off and replaced by Evans on the left.
And it was a long pass from the newcomer that almost provided an equaliser just past the hour mark.
The ball was nodded down by Lowe and Pitman took one touch before hitting a neat half-volley that struck the base of the post.
Pompey were suddenly looking a real threat and when Sunderland failed to deal with another Evans delivery, Thompson was unable to find the target at the back post.
Lowe then had a great opportunity following good work from Pitman, but rolled his shot wastefully past the post.
Jackett made his second switch to the forward line on 69 minutes, as Bogle made way for Hawkins.
The striker was soon having his shirt tugged inside the area, although Whitestone did not think it was enough to warrant a penalty.
Evans then did well to hold off a challenge and burst forward, firing in a long-range strike that flashed past the post.
But Pompey did find themselves level on 82 minute – and the goal came from a very unlikely source.
THOMPSON had yet to score in 69 appearances, but certainly picked the right location to open his account, nodding home after Evans had collected the ball from Clarke and sent it into the box.
The Blues contingent of an EFL Trophy record crowd of 85,021 erupted as the players ran towards them in celebration.
It had been a dominant second half display, but Sunderland might have secured victory in stoppage-time when Denver Hume skipped through and sent a dangerous ball across the face of goal.
Full Time: Pompey 1 Sunderland 1
There were, unsurprisingly, a few tired legs on display at Wembley as the extra period of 30 minutes got started.
Pompey were still looking to get forward and Evans was tackled inside the box after playing a neat one-two with Brown.
Lowe then screwed a shot wide after Hawkins had laid the ball off, while an angled effort from Brown was comfortable for McLaughlin.
Following a brief break after the first set of 15 minutes, the Blues got straight back on the attack and Evans had a shot blocked after cutting in from the left.
Jackett was forced to make a change when Ben Close limped off and his replacement almost scored within seconds of coming on.
Anton Walkes received the ball on the edge of the box and his effort had to be clawed behind by McLaughlin.
But Pompey did go ahead on 114 minutes and it was a brilliant finish from LOWE, who collected a long Clarke pass and sent a glorious lob over McLaughlin and into the net.
The winger was booked for taking his shirt off in celebration, but it looked like being the decisive goal.
Sunderland had other ideas, however, and in the dying seconds McGeady scrambled home an equaliser, despite the best efforts of Clarke to clear from the line.
After Extra Time: Pompey 2 Sunderland 2
A penalty shoot-out is always a nervy occasion, but the Blues kept their nerve throughout, scoring all five of their spot-kicks.
Evans, Pitman, Brown and Lowe all tucked away their efforts, while Sunderland’s second from Cattermole was saved by MacGillivray.
It meant that Hawkins had the chance to win it for the Blues and he made no mistake, slotting the ball home to send the large travelling contingent home in joyous mood.
Pitman then led his side up the Wembley steps to collect the Checkatrade Trophy and send those fans wild with delight.
Pompey (4-2-3-1): MacGillivray; Thompson, Burgess, Clarke, Brown; Naylor, Close (Walkes 113); Lowe, Pitman (c), Curtis (Evans 56); Bogle (Hawkins 69)
Goals: Thompson 82, Lowe 114
Booked: Curtis, Evans, Lowe
Subs not used: Bass, Haunstrup, May, Vaughan
Sunderland (4-2-3-1): McLaughlin; O’Nien, Flanagan, Baldwin, James (Hume 88); Leadbitter (Wyke 95), Cattermole; Morgan (Gooch 73), Honeyman (c), McGeady; Grigg (Power 77)
Goals: McGeady 38, 119
Booked: Baldwin, McGeady
Subs not used: Ruiter, Dunne, McGeouch
Referee: Dean Whitestone