Pompey’s long wait for a league win continued as they were beaten at Bolton for the second time in a week.
Dion Charles gave the home side an early advantage and the Blues struggled to find a response at the other end of the pitch.
Kieran Lee made the task even harder straight after the break before Eoin Toal made sure of all three points for Wanderers.
Simon Bassey made six changes from the side narrowly beaten at the same venue in the Papa Johns Trophy a few days earlier.
With Josh Griffiths being recalled by West Brom, Josh Oluwayemi was handed a League One debut between the sticks.
There were also returns for Michael Morrison, Ryan Tunnicliffe, Owen Dale, Michael Jacobs and Colby Bishop.
Marlon Pack was suspended and Josh Koroma sent back to Huddersfield, while Ronan Curtis, Dane Scarlett and Joe Pigott all dropped to the bench.
They were joined among the substitutes by new signing Ryley Towler and teenage keeper Toby Steward.
Pompey were forced to deal with some early Bolton pressure and Oluwayemi did well to keep out Conor Bradley’s neat flick.
The keeper gathered another effort from the same player moments later after Kyle Dempsey’s initial attempt had been blocked by Joe Morrell.
But the hosts did take the lead on 15 minutes, with the Blues not reacting quickly enough after Charles’ initial effort had been blocked.
Randell Williams sent the ball straight back into the mixer and Charles was left alone to fire it into the net.
Pompey started to improve as the first half progressed, although were struggling to create any meaningful chances.
The best of them fell to Morrison when he found space to meet a Jacobs corner, but the defender could only send his header past the post.
They finished the half on top and were certainly producing plenty of effort, with Wanderers remaining resolute at the back to keep them at bay.
Half Time: Bolton 1 Pompey 0
The visitors needed a strong start to the second period, but instead found themselves further behind within three minutes of the restart.
Oluwayemi could not keep hold of Dempsey’s cross from the right and Lee rifled the ball into the net.
The keeper did better moments later, though, getting down to his right to keep out a volleyed effort from Charles.
Pompey were trying to find a way back and a shot from Bishop at least forced James Trafford into action just past the hour mark.
The hosts immediately went closer at the other end, though, with Oluwayemi getting down to his right to keep out Dan Nlundulu’s header.
Bassey made a triple switch on 66 minutes, as Towler, Curtis and Reeco Hackett were brought on for Morrison, Jacobs and Denver Hume.
But it failed to halt the Wanderers charge and Toal soon extended their advantage further, arrowing the ball home after exchanging passes with Bradley on the edge of the box.
Louis Thompson and Scarlett were both brought on for the closing stages, as Tunnicliffe and Bishop made way.
The Blues were unable to mount an unlikely late comeback, however, as their run of poor form continued.
Bolton (3-4-1-2): Trafford; Toal, Aimson, Johnston (Santos 83); Bradley, Dempsey (Sheehan 83), Morley, R.Williams; Lee (c) (M.Williams 75); Charles (Kachunga 75), Bödvarsson (Nlundulu 37)
Goals: Charles 15, Lee 48, Toal 71
Subs not used: Beck, Sadlier
Pompey (3-4-3): Oluwayemi; Morrison (Towler 66), Raggett (c), Ogilvie; Swanson, Tunnicliffe (Thompson 83), Morrell, Hume (Hackett 66); Dale, Bishop (Scarlett 83), Jacobs (Curtis 66)
Booked: Morrell
Subs not used: Steward, Pigott
Referee: Geoff Eltringham
Attendance: 17,977 (975 Pompey fans)