Paul Cook’s return to Fratton Park ended in defeat after Portsmouth came from a goal down to beat the Blues 2-1. James Norwood netted his seventh goal of the season to give the Blues the lead on 32 but Pompey skipper Tom Naylor headed a leveller four minutes before the break and then Marcus Harness grabbed the winner in the 72nd minute.
Town boss Paul Cook made four changes with Norwood, Stephen Ward, Teddy Bishop and Keanan Bennetts returning to the side.
Ward came in at left-back for Myles Kenlock, who was left out of the 18 and Bishop in central midfield for Cole Skuse, who was on the bench.
Bennetts replaced Troy Parrott but playing in a very advanced left-sided position rather than a number 10 with the on-loan Tottenham man on the bench.
Alan Judge moved into a third central midfielder’s role towards the left, although ahead of Bishop and Andre Dozzell. Norwood returned in the out-out-out striker’s role with Kayden Jackson also dropping to the bench.
Kane Vincent-Young was among the subs for the first time in 17 months following his injury problems, while Mark McGuinness and Armando Dobra were also on the bench for the first time since the change of manager.
Jack Lankester, Josh Harrop and Aaron Drinan missed out on places in the 18 having been on the bench for Tuesday’s 2-0 defeat at Fleetwood.
Portsmouth, with new management team Danny and Nicky Cowley in the dugout for the first time following their appointment yesterday, made two changes from the side which lost 1-0 at Peterborough in midweek.
Marcus Harness and Jordy Hiwula came into the XI for Ben Close and Rasmus Nicolaisen, whose own goal settled the game at London Road.
Town wore last year’s burgundy and blue away shirt but with blue shorts with a yellow and burgundy trim and yellow socks.
Prior to kick-off the players and officials both took a knee in support of Black Lives Matter, again with the exception of Toto Nsiala.
Pompey struck the game’s first shot in the fourth minute, Ronan Curtis hitting a 30-yard free-kick which wobbled in the air but was claimed comfortably by Holy.
Town attacked for the first time in the 11th minute when Bishop won the ball on halfway, Bennetts fed Edwards to the right and the Welshman’s chipped cross to the far post was nodded into the side-netting by Norwood having already appeared to have gone out of play.
Two minutes later, Norwood hooked a ball over the Portsmouth backline for Edwards, who was eventually outmuscled by Lee Brown.
Following Tuesday’s lackadaisical display at Fleetwood, manager Cook was constantly barking at his midfield and strikers to press whenever Pompey had the ball in their area of the field, and the cajoling appeared to be having some impact with the Blues having more bite than they had at Highbury.
Referee Alan Young showed his first yellow card of the day in the 18th minute when Jack Whatmough pulled back Bennetts as the on-loan Borussia Mönchengladbach man was about to shoot from 25 yards.
Judge took the free-kick and curled the ball to keeper Craig MacGillivray’s left and the keeper did well to get across to it and push it wide and to safety.
Town, playing at a greater tempo than at Fleetwood and seeing much more of the ball, were working themselves into some promising positions in the Pompey half, while at the other end Portsmouth’s rather fewer forays forward had been snuffed out.
On 29, a corner was worked to Bishop not far outside the area but the midfielder’s shot hit a Pompey defender and flicked through to MacGillivray.
The Blues went closer a minute later when Norwood was played in on the right of the area and cut across to Bennetts but the winger was unable to get a touch and keeper MacGillivray claimed.
But Town didn’t have to wait too much longer for a goal. On 32 Edwards played a clever pass for Norwood in the same area of the box and the striker smashed a powerful shot across MacGillivray and into the net for his seventh goal of the season.
The Blues deserved their lead having been the better side but appeared less attack-minded in the minutes following their goal and in the 41st minute the home team levelled.
Pompey had hardly looked threatening until Curtis sent over a corner from the left and skipper Naylor battled his way to the ball and headed home off the inside of the far post.
Having got back on terms, Portsmouth ended the half the stronger and on 43 Curtis curled a shot wide.
Town would have been good for their half-time lead had they not conceded the goal shortly before the break. They’d looked a much better outfit than on Tuesday and deserved their goal - a second in three games from open play - which was cleverly worked by Edwards and finished comprehensively by Norwood.
Pompey had reacted well to the Town goal but hadn’t looked like grabbing a goal until Naylor’s header from Curtis’s very-difficult-to-defend corner.
Three minutes after the restart Edwards again played Norwood in, this time breaking towards the edge of the area but the Blues striker was unable to get enough on it and MacGillivray was able to claim.
A minute later, Naylor won another header from a corner, Holy blocked, the ball dropped loose and after a brief scramble eventually ended up in the big Czech’s hands.
Soon after, Curtis was booked for a foul as Bishop broke into the Pompey half, then on 56 Andy Cannon joined him for a foul on Edwards on the right wing. Two minutes later, midfielder Cannon was swapped for Close.
A minute later, Pompey broke through Harness and Ryan Williams struck a shot across the face of goal.
On 59 Town swapped Bennetts, who had been less effective since the break, for Dobra, with the Albanian U21 international making his first appearance under new boss Cook. Dobra moved into a number 10 role with Judge in a more orthodox left-sided position.
Edwards was booked for a foul on Curtis in the 66th minute as Portsmouth broke following a Town corner which had come to nothing. Pompey complained that they would have been better off had the official played the advantage and with the resultant free-kick looping into Holy’s arms, they may have had a point.
Town had threatened very little since the break but on 70 a Dozzell free-kick found Norwood and his header from just inside the box inched just past the post having caught a Pompey defender. A minute later, Bishop was booked for a foul on Close.
Chances at both ends had been rare since half-time but in the 72nd minute the home side went in front.
Portsmouth broke down the left having played out from the back - although with Town players feeling the ball had gone out of play - and eventually Curtis's cross reached Harness bursting into the area from the other flank. The former Burton winger’s first shot was blocked by Judge but with his second he made no mistake.
In the 79th minute Town made a double change with Vincent-Young making his very long-awaited return and Jackson coming into a two-man attack. James Wilson and Judge made way. Chambers moved to centre-half to allow Vincent-Young to take up his usual right-back role, while Dobra switched to left wing.
Jacobs was booked for a foul on Dobra in the 82nd minute but with Town not looking particularly like levelling. On 88 Parrott took over from Bishop.
In the final scheduled minute Pompey might have added a third but a low ball across the edge of the six-yard box was bundled behind by Nsiala.
Soon after the fourth official’s board had indicated five additional minutes, James Bolton headed powerfully straight at Holy following the resultant corner.
Pompey were looking more likely to score a third goal than Town a second as referee Young brought the game to an end to cheers from the home bench and directors’ box as new manager Cowley recorded his first win in his opening game in charge.
In the end, Portsmouth deserved the win with the Blues having shown little in the second half. The pressing and work-rate which had been on display in the first half perhaps suffered due to tiredness as the game wore on and although chances had been few and far between at both ends, when a decent opportunity came, Harness took it.
The Blues, who dropped to ninth following the later fixtures, now have a free midweek in which manager Cook plans extensive work on the training field ahead of next Saturday’s trip to another of his old clubs, Wigan.
Ipswich: Holy, Chambers (c), Nsiala, Wilson (Vincent-Young 79), Ward, Dozzell, Bishop (Parrott 89), Bennetts (Dobra 59), Edwards, Judge (Jackson 79), Norwood. Unused: Cornell, McGuinness, Skuse.
Portsmouth: MacGillivray, Bolton, Whatmough, Raggett, Brown, Williams, Naylor (c), Cannon (Close 58), Curtis, Harness, Hiwula (Jacob 72). Unused: Ward, Nicolaisen, Daniels, Mnoga, Byers. Referee: Alan Young (Cambridgeshire).