Pompey’s barren start to 2018 continued as they suffered a narrow defeat to high-flying Shrewsbury at a damp Fratton Park.
James Bolton was left in space to score the only goal of the game midway through a first half that failed to sparkle.
But there was plenty of controversy before the break, with two decent shouts for a penalty turned down.
The Blues looked more inventive following the interval, but keeper Craig MacGillivray and the woodwork came to the Shrews’ rescue.
Adam May’s late dismissal for a second bookable offence only served to compound the hosts’ misery.
Kenny Jackett made three changes from the side that suffered a dramatic defeat at Rotherham the previous week.
Gareth Evans returned from injury to skipper the side, while there were also recalls for May and Oli Hawkins.
Regular captain Brett Pitman dropped to the bench, along with Sylvain Deslandes and Matty Kennedy.
Pompey were guilty of some sloppy play before the break, although the wet conditions were undoubtedly making life tough for both sides.
But they dominated possession throughout the first half and Hawkins could not quite connect with Evans’ cross after leaping in the box.
May then received the game’s first booking for a late challenge on Shaun Whalley as the contest continued to meander.
And the goal that gave Shrewsbury the lead was indicative of what had come before, as the Blues failed to deal with a corner and Bolton took advantage at the far post.
There might have been a second when Luke McGee lost out in a race for the ball with Abu Ogogo, but Ben Close was on hand to clear the danger.
But the hosts were soon back on the attack and when Close’s free-kick was only partially cleared, Donohue’s follow-up volley was deflected wide.
Pompey were even closer to a leveller on 31 minutes, as Hawkins met Evans’ delivery, only for MacGillivray to make a superb save.
There was controversy either side of that, however, as the hosts were controversially denied a penalty on two occasions.
Referee David Coote had a clear view of Christian Burgess’ shirt being tugged as he tried to attack a corner, but opted to do nothing.
The official then failed to spot Whalley’s handball in the box, much to the fury of the home side, who rushed to complain, earning Evans a booking.
The Blues had to put that to the back of their minds and Hawkins almost capitalised when the Shrews defence failed to deal with May’s pass.
Evans also had a shot blocked by Omar Beckles and another effort that went over, as the hosts went in behind at the break.
Shrewsbury Town 1
Former Fratton favourite Ricardo Rocha – who made almost 100 appearances for the club – was introduced to the crowd during the interval.
That provided a lift, but the supporters were soon up in arms again when Coote missed another handball, although at least this one was not in the box.
Pompey were still struggling to find any fluidity and Jackett soon made a switch, replacing Jamal Lowe with Pitman.
That certainly provided the required spark, as the hosts soon began to take control and had a series of chances to draw level.
Toto Nsiala was well-placed in the box to keep out Evans’ shot and when the skipper delivered the ball back into the box, Pitman’s guided header was saved by MacGillivray.
Matt Clarke then saw an opening from the resulting corner, but could not force the ball through a sea of orange shirts.
And MacGillivray came to Shrewsbury’s rescue once again when he dived to his right to expertly keep out Kal Naismith’s 30-yard drive.
But the chances began to dry up again and so Naismith was withdrawn on 70 minutes for the fresh legs of Connor Ronan.
It was not all one-way traffic, though, and McGee managed to claw away Carlton Morris’ header at point-blank range.
Whalley then arrowed an angled drive narrowly past the post after Shrewsbury had countered quickly.
Time was rapidly running out for the hosts, but they almost found an equaliser on 84 minutes.
Ronan’s looping header was volleyed towards goal by Pitman and a deflection took the ball onto the crossbar.
And there was more controversy late on when the ball bounced up and hit the arm of Beckles, only for Coote to remain unmoved.
But there was still time for the afternoon to get even worse for the hosts, as May’s foul on Stefan Payne saw him receive a second yellow card and subsequent red.
Pitman almost rescued an unlikely point deep into stoppage-time, however, with an angled shot rolling agonisingly past the post.
Pompey (4-2-3-1): McGee; Thompson, Burgess, Clarke, Donohue; May, Close; Evans (c), Naismith (Ronan 70), Lowe (Pitman 55); Hawkins
Sent off: May (two yellow cards)
Booked: Evans, Donohue
Subs not used: Bass, Deslandes, Bennett, Kennedy, Chaplin
Shrewsbury (4-1-4-1): MacGillivray; Bolton, Nsiala, Sadler, Beckles; Godfrey; Whalley (John-Lewis 90+2), Nolan, Ogogo (c), Rodman; C.Morris (Payne 83)
Goals: Bolton 21
Booked: C.Morris, Rodman, Payne
Subs not used: Rowley, Hendrie, Lowe, B.Morris, Gnahoua
Referee: David Coote
Attendance: 17,779 (498 away fans)
Chaplin, Main, Smith and May on target
Pompey eased to victory in their penultimate pre-season test against Isthmian League outfit Bognor at Nyewood Lane.
They created plenty of openings before the break, with Conor Chaplin and Curtis Main both finding the target.
Harvey Whyte reduced the deficit early in the second half, but Michael Smith then scored from the spot before Adam May wrapped things up.
Chaplin started particularly brightly and after one early shot was saved, Ben Close wastefully fired over the bar.
He was then sent through on goal, but Billy Granger was quickly off his line to make a crucial save.
The Rocks keeper was almost single-handedly keeping the Blues at bay and made another key stop to deny Ben Tollitt from long-range on 15 minutes.
Main was next to try to break the deadlock, but could not find the target after Christian Oxlade-Chamberlain had laid the ball into his path.
It was Chaplin with another go on 19 minutes and his deflected shot was heading for the net until Granger showed superb reflexes to divert it over the bar.
Tollitt’s set-piece delivery was also causing trouble, with Amine Linganzi and Tom Davies not quite able to take advantage.
Pompey finally got the goal their attacking dominance deserved on 23 minutes after CHAPLIN was brought down just outside the box.
The teenage forward stepped up to take the free-kick and expertly curled it over the wall and beyond Granger’s grasp.
Bognor then enjoyed their best spell of the game and should really have bagged an equaliser.
Paul Jones did well to deny Dylan Barnett from point-blank range and when the ball popped up nicely for James Fraser, he could only fire against the woodwork.
Pompey then made the hosts pay for their profligacy just before the break, as MAIN got above his marker to convert Chaplin’s teasing cross.
Bognor Regis Town 0
Jones was called into action early in the second half, flinging himself to the right to keep out Barnett’s effort.
But he was unable to keep hold of the ball from the resulting corner, giving Whyte the chance to poke home.
The chances were not arriving as frequently as they had before the break, although one good move involving May and Main ended with Close firing over.
Paul Cook gave his two scorers a breather just past the hour mark, as Main and Chaplin made way for Smith and trialist Dean O’Halloran.
And it was SMITH who restored the Blues’ two-goal lead on 67 minutes, sending substitute stopper Joe Taylor the wrong way from the penalty spot after Darren Budd had brought down Tollitt.
The game was meandering towards its conclusion, but MAY livened things up again with a fourth goal, driving a 25-yard shot into the bottom corner.
A couple of academy starlets entered the fray late on and Tommy Scutt came close to adding his name to the scorers, meeting Theo Widdrington’s cross and volleying into the side netting.
And Oxlade-Chamberlain denied the Rocks a late consolation when he cleared Jimmy Wild’s drive from the line.
Bognor (4-3-3): Granger (Taylor 56); Crane, Field (Wollers 70), El-Abd (Sanders 56), Barnett; Whyte (Budd 56), Beck (c) (Robinson 81), Tuck (Consaro 70); Davies, Pearce (Penfold 81), Fraser (Wild 56)
Goals: Whyte 48
Pompey (4-diamond-2): Jones; Oxlade-Chamberlain, Davies, Barton (c), Widdringron; May, Linganzi (Yates 69), Tollitt, Close (Scutt 75); Main (Smith 62), Chaplin (O’Halloran 62)
Goals: Chaplin 27, Main 43, Smith 67 (pen), May 74
Sub not used: Bass
Referee: Tim Robinson
Plenty of goals for Macca benefit
Pompey twice led against Bournemouth in Alan McLoughlin’s benefit match, but had to settle for a 3-3 draw in the only Fratton friendly of the summer.
Gary Roberts fired the hosts into an early lead and although Lewis Grabban levelled, Michael Smith immediately restored the advantage.
But the usual flood of second half substitutions left the Blues a bit ragged, with Jordan Ibe and Dan Gosling appearing to secure victory for the Premier League visitors.
There was still time for Adam May to snatch a late leveller, however, and cap an entertaining afternoon on the sunny south coast.
The man of the moment greeted the crowd before kick-off and received warm applause from the Fratton faithful.
It was the visitors who were first to threaten once the game got underway, with Alex Bass getting down low to keep out Ryan Fraser’s drive.
But the Blues broke the deadlock after just five minutes, courtesy of a fine effort from ROBERTS.
The midfielder collected a pass and showed fancy footwork to beat Simon Francis before curling the ball into the bottom corner.
Pompey were passing the ball around nicely and Rhoys Wiggins did well to stop Smith getting a shot away after a corner had only been partially cleared.
But the Cherries soon started to settle and Grabban drilled inches past the post after being teed-up by Lewis Cook.
Roberts came close to scoring again at the other end, this time curling wide after playing a neat one-two with Carl Baker.
It was Bournemouth who got the next goal on 24 minutes, however, as Fraser burst into the box and cut the ball back for Grabban to slide past Bass.
But it took the hosts just a minute to restore their lead, with SMITH on hand to calmly stroke home after Enda Stevens’ effort was deflected into his path.
The Cherries tried to restore parity and an acrobatic effort from Marc Pugh was deflected behind before the same player headed over at the far post.
As well as enjoying an entertaining contest on the pitch, the crowd were keen on showing their support for a certain former player, with chants of ‘Alan McLoughlin’ and ‘sign him up’ ringing out.
AFC Bournemouth 1
Paul Cook introduced a couple of trialists for the second half, with Chris Konopka taking over between the sticks and Amine Linganzi coming on soon after the restart.
But it was a contracted player who threatened for Pompey, as Smith had a shot deflected behind before heading over from the resulting corner.
Cherries substitute Joshua King had the ball in the back of the net before then, but his celebrations were interrupted by the linesman’s flag.
The changes kept flowing and Noel Hunt was denied by a superb Adam Federici save from point-blank range after Roberts had sent a teasing cross into the box.
But the Cherries found themselves level on 70 minutes when Ibe dropped his shoulder and finished at the near post.
Pompey came close to restoring their advantage once more when Hunt charged down Federici’s clearance, only for the keeper to recover and deny his opponent from a tight angle.
The Cherries forged ahead for the first time on 79 minutes, though, as Wiggins squared for Gosling to poke in from close range.
With Cook changing the entire squad, the Blues had lost their shape somewhat, but there was still time for MAY to scramble home an untidy late equaliser.
Pompey had shown plenty of encouraging moments against their top-flight visitors and, more importantly, the fans were able to pay tribute to a Blues legend.
Thanks for the memories, Macca
Pompey (4-2-3-1): Bass (Konopka 46); Talbot (May 82), Whatmough (Davies 78), Burgess (Barton 78), Stevens (Haunstrup 78); Rose (Hunt 61), Doyle (c) (Close 69); Baker (Oxlade-Chamberlain 80), Roberts (Tollitt 80), Lalkovic (Linganzi 52); Smith (Main 61)
Goals: Roberts 5, Smith 25, May 88
Subs not used: Bennett, Chaplin
Bournemouth (4-2-3-1): Federici; O’Kane, Francis (c), Daniels, Wiggins (Butcher 84); Cook (MacDonald 46), Arter; Fraser (Ibe 46), Grabban (Mousset 46), Pugh (Gosling 46); Wilson (King 46)
Goals: Grabban 24, Ibe 70, Gosling 79
Subs not used: Stanton, Cornick, Jordan, Harfield, Buckley, Lee, Travers
Referee: James Linington
Attendance: 5,153 (531 away fans)
After the disappointment of the play off defeat Paul Cook has started to trim the squad for next season.
Brian Murphy, Chad Field and Snorre Nilsen have been released following the expiration of their contracts.
Adam McGurk, Kal Naismith and Matt Tubbs have been transfer listed. Options taken up on Tollitt, May and Close. Talks continue with Hollands and Davies.
Good to see Tollitt kept, the only real surprise in Naismith who was just starting to show some promise.