Pompey were narrowly beaten by Bristol City at Fratton Park in their final pre-season friendly of the summer.
Mark Sykes precisely volleyed home early in the second half to secure victory for the Championship side.
But the Blues showed glimpses of promise – particularly after the break – and there were a host of first home outings for the club’s summer signings.
A minute’s applause was held before kick-off in memory of former Pompey outside-right Tony Priscott, who passed away earlier this month at the age of 82.
The hosts made a bright start under the south coast sunshine and posed some early questions for their opponents.
But the Robins thought they had broken the deadlock on 11 minutes, when Sam Bell turned home a low cross from former Fratton loanee Cam Pring.
The forward had strayed into an offside position at the back post, however, and the flag was quickly raised.
Pompey were getting the ball in some dangerous areas as the first half progressed, without being able to test Max O’Leary between the sticks.
And they almost fell behind on 22 minutes, as Nahki Wells met an Alex Scott delivery and nodded against the post.
The keeper also did well to grab a Bell centre low down, with Harry Cornick ready to pounce just beyond him.
There was not too much else to report as the interval approached, although referee Sunny Gill rightly ignored Pring’s penalty appeals following a good challenge by Gavin Whyte inside the area.
Half Time: Pompey 0 Bristol City 0
The visitors made seven changes at the break and Pompey tried to hit them before they could properly settle.
Anthony Scully swivelled smartly to get into a shooting position and finally called O’Leary into meaningful action.
But it was the Robins who broke the deadlock on 50 minutes as a Haydon Roberts corner was not cleared and Sykes volleyed into the bottom corner.
Both sides were looking dangerous going forward and a fine Tom Lowery cross was nodded away before it could be converted by Scully at the back post.
John Mousinho made a couple of changes just past the hour mark, with Kusini Yengi and Zak Swanson on for Colby Bishop and Joe Rafferty.
The lively Scully then sent a teasing delivery across the face of goal, but it was just beyond the onrushing Yengi.
That was the winger’s last contribution, though, as he was soon replaced by fellow newcomer Abu Kamara.
It was almost the perfect introduction for the Norwich loanee, but Lowery’s cross was just too high and he could only divert the ball wide.
Four more changes followed on 77 minutes, with Sean Raggett, Ryley Towler, Jack Sparkes and Christian Saydee all given a run-out.
Bristol City then had a chance to double their advantage, only for a well-placed Matty James to fire narrowly over the bar.
And it took a superb save from Norris to claw away Raphael Araoye’s close-range header after the substitute had connected with a corner.
There was a late chance for the hosts to grab a leveller when Yengi met a Connor Ogilvie cross, but the ball was deflected behind and the corner came to nothing.
Pompey (4-3-3): Norris; Rafferty (Swanson 63), Poole (Raggett 77), Shaughnessy (Towler 77), Ogilvie; Lowery (Saydee 77), Pack (c), Morrell (Devlin 87); Whyte (Sparkes 77), Bishop (Yengi 63), Scully (Kamara 70)
Subs not used: Schofield, Stevenson
Bristol City (4-2-3-1): O’Leary; Tanner (Leeson 64), Vyner (c) (Knight-Lebel 64), Dickie (Araoye 64), Pring (Roberts 46); Knight (Sykes 46), King (James 46); Cornick (Weimann 46), Scott (Williams 46), Bell (Mehmeti 46); Wells (Conway 46)
Goals: Sykes 50
Sub not used: Wiles-Richards
Referee: Sunny Gill
Attendance: 7,986 (1,802 away fans)