Town’s hopes of a Wembley final in the Papa Johns Trophy ended at the round-of-32 stage after a 2-0 defeat to Portsmouth at Portman Road. Dane Scarlett hit the opener in the 43rd minute, profiting from some sloppy play after Town had dominated the first half and the Blues huffed and puffed after the break without finding a leveller before Zak Swanson added the second deep in injury time.
Panutche Camara and Greg Leigh both started for the Blues as boss Kieran McKenna made seven changes from the team which won 2-0 at Exeter on Saturday.
Vaclav Hladky was in goal with Richard Keogh coming into the centre of the backline with George Edmundson on the left and Luke Woolfenden on the right.
Kane Vincent-Young was on the right and Leigh, making his first appearance since his compression fracture of his leg, was on the left.
Skipper Sam Morsy and Cameron Humphreys were the central midfield pairing with full Town debutant Camara and Marcus Harness, facing his old club, behind lone central striker Kayden Jackson.
Pompey also made seven changes with ex-Blues loanee Ryan Tunnicliffe, Josh Oluwayemi, Kieron Freeman, Bury St Edmunds-born Michael Morrison, who skippered, Denver Hume, Reeco Hackett and Ronan Curtis all starting.
Town went close to going in front in only the second minute. Harness laid the ball back to Morsy on the edge of the box on the right and the Egyptian international chipped a cross to the far post where Leigh dived in to head goalwards only to find Pompey keeper Josh Oluwayemi in his way.
The Blues threatened again in the fourth minute, Camara winning a tackle on the right of the area and Harness crossing for Jackson, who helped the ball towards goal from a tight angle but Oluwayemi again saved.
A minute later, Harness brought the ball forward before striking a 25-yard effort which smashed against Camara.
Town continued to dominate and in the 10th minute, Leigh crossed from the left to Vincent-Young beyond the far post. The former Colchester man was unable to take the ball down cleanly but it fell to Jackson, who turned a shot over the bar.
Portsmouth struck their first shot of the game two minutes later, but Owen Dale’s effort flew well wide of Hladky’s right post.
On 19, Hackett was played in on the right of the box, checked back and hit a low cross which Hladky claimed comfortably.
A minute later, as Town attacked, Harness went down with what looked like a knee injury after a challenge midway inside the visitors’ half.
After treatment, the forward was led off the pitch on the far side and gingerly made his around the perimeter to the tunnel, adding to the Blues’ already considerable injury concerns.
On 24 Zanda Siziba replaced him, making his sixth senior appearance and his second from the bench in the Papa Johns Trophy this season.
The majority of the game was still being played in and around Portsmouth’s area and four minutes later Oluwayemi juggled a cross from the right but the ball failed to fall for Leigh.
As the half moved into its final 15 minutes, Leigh, who had enjoyed an impressive return, stood up a cross from the left. It was just too high for Jackson, who may have left Camara unsighted and the Guinea-Bissau international headed wide when he should have scored.
In the 35th minute, after a spell in which the Blues had shown some hesitancy in passing out from the back and Portsmouth had spent time in the Town half, Siziba shot just over from the edge of the area after Jackson had laid the ball back to him having been sent away by Humphreys and pushed wide by Morrison.
On 39, Portsmouth broke following a Town attack and Dale hit a 20-yard shot through to Hladky.
Three minutes later, Pompey went in front. Edmundson played a sloppy pass into the path of Dale, allowing him a run towards the Town goal on the right. The former Rangers man got back to hold the Crewe man up, but he played the ball across the box to Scarlett on the left, who picked it up as Woolfenden slipped and then hit a low shot beyond Hladky and into the net off the inside of the post.
The visitors might have scored a second as the half moved into injury time, Keogh this time surrendering possession and allowing Reeco Hackett to burst forward on goal before cutting inside to Dale, whose shot was well stopped by Hladky.
Pompey had another chance soon afterwards when Scarlett was found in space to the right but his chip didn’t have enough height to beat Hladky, who again saved.
There was still time for Town to claim a penalty for handball after Vincent-Young brought the ball back into the area after an Edmundson shot was blocked. Seconds before the whistle, Morsy was booked for a foul on Scarlett.
Having been on top and well in control for the most part, Town’s performance had unravelled in the final few minutes and Portsmouth could conceivably have gone in three goals in front rather than just the one.
Having given away the goal, which was the result of an error and then a slip, Town seemed to completely lose their composure at the back, gifting possession to the visitors and allowing them two more chances which Hladky did well to save.
Prior to that, the Blues had been in well charge with Leigh’s early effort and Camara’s header their best opportunities.
Town made a shaky start to the second period with Humpreys sliding in to make a challenge on Scarlett on the edge of the box after the Blues had again given the ball away.
On 49, Dale struck a shot through to Hladky with the visitors making the better start to the half.
The Blues started to show some signs of regaining control and in the 51st minute, Vincent-Young cut inside to Camara, who might have shot but instead moved the ball on and possession was lost.
Portsmouth weren’t too far away from making it 2-0 in the 55th minute when Hackett crossed from the right and Morrison’s header looped over the bar from a tight angle at the far post.
As the hour approached, Morrison was booked for time-wasting as he took a free-kick in the Pompey half, subsequently wasting more time by handing the responsibility to Oluwayemi, who had to make his way up field from goal.
Dale was booked on 61 for a foul on Siziba and might have been lucky not to be shown two cards having kicked the ball away.
While Town, who had been in charge and looking to work openings, prepared to take the free-kick, they switched Leigh and Woolfenden for Wes Burns and Cameron Burgess with the Welshman going wide on the right as Vincent-Young swapped flanks.
Four minutes later, after Scarlett had tried unsuccessfully to catch Hladky off his line from halfway, Pompey made four changes, Colby Bishop, Swanson, Sean Raggett and Clark Robertson replacing Conor Ogilvie, Jay Mingi, Hackett and Kieron Freeman.
Town were huffing and puffing as the game moved into its final 20 minutes and not looking particularly likely to find the equaliser.
On 75 youngster Albie Armin replaced Camara and moved into a holding midfield role with Morsy and Humphreys ahead of him.
Two minutes later, the ball was looped into the box for Humphreys but Morrison got in front of him to clear the danger. In the 79th minute, Pompey replaced Scarlett with Josh Koroma, who was booked for a foul on Siziba within two minutes of being introduced.
As the match moved into its final five minutes, Hladky rushed off his line to beyond midway in the half and challenged with Koroma, who picked up the loose ball. However, the former Huddersfield man only managed to find Keogh with his pass with goal at Pompey’s mercy.
A second Portsmouth goal was looking as likely as a Town first, if not more so, and on 88 Koroma shot into the side-netting from the left with Burgess by now operating as an emergency striker, as he previously did in the Cheltenham match.
In the final scheduled minute, with the Blues now laying siege to the Portsmouth penalty area, Vincent-Young cut in from the left and hit a shot which was blocked.
Moments into five minutes of injury time, Town should have been awarded a penalty. Edmundson played a superb ball in behind Hume, who clearly clipped the Wales international as he ran round the outside of the former Sunderland full-back. But referee Tom Nield waved away vociferous Blues protests from both the pitch and the stands.
After a break while Oluwayemi underwent, a Burns cross from the right flashed across the area, then Pompey sealed their placed in the last 16 with their second goal.
With Town having everyone pushed forward, Koroma and fellow sub Swanson broke away two against one and the latter slipped the ball past the advancing Hladky.
The referee’s whistle ended the Blues’ Papa Johns Trophy involvement soon afterwards after a disappointing night from Town.
Having surrendered the lead in their slack spell just before the break, the Blues never really created the clear-cut chance which might have led to a leveller - although they were denied what looked a cast iron penalty late on - with Portsmouth defending resolutely and at the end were caught on the break for the second.
As frustrating as the cup exit is, the competition was never considered a priority and perhaps a bigger concern is Harness having suffered his injury in the first half with the promotion-pushing Blues already having a number of players on the sidelines.
Town: Hladky, Keogh, Woolfenden (Burgess 62), Edmundson, Vincent-Young, Morsy (c), Camara (Armin 75), Leigh (Burns 62), Humphreys, Harness (Siziba 24), Jackson. Unused: Coleman, Agbaje, Ladapo.
Portsmouth: Oluwayemi, Hume, Ogilvie (Bishop 66), Tunnicliffe, Curtis, Freeman (Robertson 66), Dale, Hackett (Ragett 66), Scarlett (Koroma 79), Mingi (Swanson 66), Morrison (c). Unused: Griffiths, Gifford. Referee: Tom Nield (West Yorkshire). Att: 5,686 (Portsmouth 245).