Town’s FA Cup run ended at the third round stage for the sixth successive year as the 10-man Blues were beaten 2-1 by League Two Portsmouth at Fratton Park. Former Blue Gary Roberts netted a penalty in the 32nd minute, then Marc McNulty added a second five minutes later to give Pompey a comfortable 2-0 half-time lead, then after the break Ainsley Maitland-Niles pulled one back before Piotr Malarczyk was sent off for two bookable offences.
Boss Mick McCarthy named the anticipated entirely changed XI from the side which drew 1-1 with Preston on Saturday.
Bartosz Bialkowski returned in goal with Josh Emmanuel at right-back, Myles Kenlock left-back and Malarczyk and Paul Digby the centre-halves, as they were in the first game between the sides at Portman Road 10 days ago, which ended 2-2.
In midfield, Luke Hyam skippered and was joined in the centre by Jay Tabb with Maitland-Niles on the right and Tommy Oar on the left. Up front, former Pompey striker Luke Varney was partnered by Brett Pitman.
The bench featured Joe Robinson, Kyle Hammond and Shane McLoughlin, all yet to make a first-team appearance, and Adam McDonnell, whose only previous senior game for the Blues came in the Capital One Cup at Doncaster.
Portsmouth named both their ex-Town players, keeper Brian Murphy and winger Roberts, in a team featuring three changes from their team at Portman Road with skipper Michael Doyle, Gareth Evans and Christian Burgess replacing Danny Hollands, Ben Close and Adam McGurk.
The home side created the game’s first opening in the third minute when Kyle Bennett was sent in on the left of the area but hit his shot across the advancing Bialkowski and wide.
Town, wearing their orange and black third kit, threatened for the first time a minute later when Pitman reacted quickly to reach an under-powered Doyle header back towards keeper Murphy, but looped the ball on to the roof of the net.
But as in the first game the League Two side were seeing most of the ball and on nine Roberts shot straight at Bialkowski.
Malarczyk was handed the game’s first yellow card for blocking Marc McNulty in the 14th minute. Roberts slammed the freekick against the wall.
The Blues started to come more into it after the quarter-hour, Pitman’s header from Maitland-Niles’s cross from the right was diverted away, then the former Bournemouth man tried to slip Varney in on goal, but the ball caught the one-time Pompey striker’s heels.
But the home side were still having more of the ball and on 19 Bennett cut in from the left and scraped a shot wide.
Emmanuel did well to get in front of Evans on 21 as he looked to head home Ben Davies’s dangerous cross from the right.
Neither side was able to create another opportunity until the 31st minute when Barton played in McNulty but Bialkowski quickly came off his line to block.
However, the home side kept hold of the ball and got it back in the box where Roberts was scruffily felled by Malarczyk. Referee Andy Woolmer considered his decision before pointing to the spot, leading to Blues’ protests, although the Polish defender kept out of it having already been booked.
The ex-Town winger took the kick himself and Bialkowski was unfortunate not to save it, diving to his left and clawing it into the opposite corner of the net with his right hand.
Bennett hit a weak effort through to Bialkowski, before the home side increased their lead in the 37th minute. Evans drifted a cross over from the right and McNulty placed a header past the Blues keeper from six yards.
Having gained their two-goal lead Portsmouth had their tails very much up and were continuing to take the game to the lacklustre Blues. Just before half-time, McNulty was threaded in on goal but Bialkowski came off his line quickly to claim.
The home side were good for their two-goal lead at the break having created the game’s best opportunities - Pitman’s early moment of opportunism the nearest the Blues came to a goal - and as at Portman Road having played the better football.
Aside from a spell in the middle of the half prior to the goals when they had been unable to create a chance, much-changed Town had been on the back foot throughout.
Five minutes after the restart, the home side almost added to their lead. Evans played in McNulty on the right of the area, beating the offside trap, according to the linesman, but saw his shot blocked by Bialkowski as he rushed off his line. The on-loan Sheffield United man looped the rebound well over.
A minute later Pompey went close again. A well-worked freekick routine on the left was played inside to skipper Doyle, whose strike flew not far wide of Bialkowski’s right post.
The home side continued to present the greater threat, Evans breaking away on 56 but shooting well over.
The Blues had made little impression on the second half when Maitland-Niles pulled a goal back out of nothing. The on-loan Arsenal man curled a superb strike into the top corner of Murphy’s net from 25 yards to claim his second senior goal.
Pompey weren’t far from restoring their two-goal advantage four minutes later when McNulty was fed in on the left of the area and cut the ball across the six-yard box, but no one was on hand to apply the final touch.
Pitman looped an ambitious effort into Murphy’s arms from well out on the right on 66 but Blues chances remained rare. On 71 Tabb was replaced in central midfield by Giles Coke.
A minute later, Varney and Pitman conjured an opportunity after an error from Burgess, the former Pompey man laying the ball back to his strike partner, who screwed his shot well over.
Larsen Touré, back after his groin problem, replaced Varney as the game moved into its final quarter hour.
A minute later, the Blues were reduced to 10 men. Roberts got away from Malarczyk midway inside the Town half and the already-booked defender caught his legs, probably inadvertently.
Referee Woolmer showed the Pole, making only his third Town start, his second yellow card of the evening and then the Blues’ first red of the season. Sub Coke moved into the back four.
In the final minute of scheduled time U21s skipper Joe Robinson was handed his senior debut in place of Maitland-Niles, taking up his usual role at the centre of the defence with Coke moving back into midfield.
Town pressed for an equaliser in injury time but Portsmouth keeper Murphy was never seriously tested and referee Woolmer’s whistle confirmed Pompey’s first victory over the Blues at Fratton Park since October 1966.
The home side thoroughly deserved the victory on the balance of both games with the Blues never really looking like getting anything out of the replay, despite Maitland-Niles’s excellent second-half goal.
A stronger Town side would almost certainly have given Pompey - who face Premier League AFC Bournemouth at home in round four - a more significant test in both games, but as manager McCarthy made clear with his line-ups, the Championship is very much his priority.
Reading’s 5-2 victory at home to Huddersfield means Town’s Championship game against the Royals set for a week on Saturday will be postponed and will be played on Tuesday 2nd February.
Portsmouth: Murphy, Davies, Webster, Burgess (Close 85), Stevens, Barton, Doyle (c), Evans, Roberts (Chaplin 82), Bennett, McNulty. Unused: Bass, May, Tollitt, Naismith, McGurk.
Town: Bialkowski, Emmanuel, Digby, Malarczyk, Kenlock, Hyam (c), Tabb (Coke 71), Maitland-Niles (Robinson 89), Oar, Varney (Touré 76), Pitman. Unused: Gerken, Hammond, McDonnell, Touré, McLoughlin. Referee: Andy Woolmer (Northamptonshire). Att: 15,179 (Town: 796).