Pompey began the new League One campaign with a narrow defeat to Shrewsbury, despite dominating possession at New Meadow.
The game was short of clear-cut chances and it took a fine second half strike from Ryan Giles to settle the contest.
And Ross McCrorie was then sent off on his debut to cap a disappointing opening day for the Blues in Shropshire.
Kenny Jackett also handed competitive starts to summer signings Paul Downing and Marcus Harness.
And there was a second Blues bow for striker John Marquis, who had a short spell on loan at the club in 2013.
Former Shrewsbury full-back James Bolton had to be content with a place on the bench, as did striker Ellis Harrison.
Brett Pitman was also named among the substitutes, so Gareth Evans claimed the captain’s armband.
It was not surprising to see a disjointed start to the action so early in the campaign, with the visitors enjoying territorial advantage, but not creating any clear-cut openings.
Downing thought he was fouled at the far post when trying to meet Lee Brown’s corner, although referee Charles Breakspear did not agree.
Pompey had a large share of the possession and were just lacking a final pass in key areas of the pitch.
McCrorie shanked a volley from the edge of the box and when the ball came back to him, the on-loan midfielder saw his second attempt gathered by Shrews stopper Max O’Leary.
The Blues were growing frustrated as the half progressed, feeling that decisions were going against them.
Shrewsbury then had a great chance when veteran striker Steve Morison controlled the ball neatly and volleyed narrowly over the bar.
Pompey were still angry about failing to get some free-kicks, leading to fouls from Anton Walkes and Gareth Evans that earned the pair bookings in quick succession.
They brightened up as half-time neared, however, and several deliveries into the area were well dealt with by O’Leary.
Marquis also had a couple of long-range shots blocked, as the hosts ensured it was goalless at the interval.
Shrewsbury Town 0
Pompey looked to get at their hosts following the restart, but were still finding it hard to test O’Leary.
A fizzing Brown cross did cause alarm when it drifted towards goal and the keeper had to palm the ball to safety.
Jackett soon decided to make a double substitution, with Evans and Anton Walkes replaced by Pitman and Bolton.
A free-kick from Brown – after Ethan Ebanks-Landell was booked for barging Marquis to the ground – was flicked on by Tom Naylor and deflected behind.
Pitman and McCrorie also received cautions for late challenges on Romain Vincelot and Shaun Whalley.
And the free-kick conceded from the second of those led to Shrewsbury opening the scoring on 68 minutes.
Giles received the ball and hit a rocket of a shot from long-range that left Craig MacGillivray helpless against his former club.
Pompey tried to hit back and Pitman instinctively stuck out a boot to meet Bolton’s cross, only to see the ball land safely in O’Leary’s arms.
And they almost found an equaliser when Brown played a clever free-kick to Marquis, who had broken away from a packed box to receive the ball.
He sent the ball towards the net, but Aaron Pierre slid in to somehow turn the ball just past his own post.
Jackett made his final throw of the dice soon after, with Harrison coming on for his debut in place of Bolton.
But the Blues were soon down to 10 men, with Breakspear deciding that McCrorie had caught Donald Love late and showing the Scot his second booking.
They threw men forward in search of a leveller, although Shrewsbury were holding firm at the back to repel them.
There was six minutes of added time to give the travelling army of Pompey fans hope of some late drama.
And it almost arrived when Brown sent a low ball across the face of goal that nobody was able to get a touch on.
A corner was then cleared only as far as an unmarked Curtis in the box, but he fired over and that proved to be the final chance.
Shrewsbury (3-5-2): O’Leary; Williams, Ebanks-Landell, Pierre; Love, Edwards (c), Vincelot, McCormick (Laurent 53), Giles; Morison (Eisa 89), Okenabirhie (Whalley 64)
Goals: Giles 68
Booked: Ebanks-Landell, Whalley, Love
Subs not used: Murphy, Beckles, Golbourne, Walker
Pompey (4-2-3-1): MacGillivray; Walkes (Bolton 53), Downing, Burgess, Brown; McCrorie, Naylor; Curtis, Evans (c) (Pitman 53), Harness (Harrison 75); Marquis
Sent off: McCrorie (two yellow cards)
Booked: Walkes, Evans, Pitman
Subs not used: Bass, Haunstrup, Close, Cannon
Referee: Charles Breakspear
Attendance: 7,880 (1,714 Pompey fans)