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.
Half Time: Pompey 2 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)