Pompey are through to the second round of the Johnstone's Paint Trophy after Bournemouth botched two of their penalties in the shootout at Fratton Park following an entertaining 2-2 draw.
A match played in front of a crowd just shy of 6,000 got off to the worst possible start for the hosts as Shaun MacDonald headed in Simon Francis' cross after just fve minutes, although a stronger hand from Mikkel Andersen would surely have kept the ball out.
The vistors dominated much of the first half, taking advantage of some sloppy defending from a new look centre back partnership of the returning Kevin Long and debutante Josh Thompson.
However, Pompey scored against the run of play at the end of the first half when Luke Rodgers turned in Mustapha Dumbuya's brilliant low cross across the the box.
Lee Williamson came off from the bench and replaced Thompson at the start of the second half with Darel Russell moving to centre back but the chances for the Cherries kept on coming.
After a couple of near-misses, Pompey did concede again when MacDonald was left completely unmarked from a corner, allowing him plenty of time to drill the ball from outside the box into the top corner of the net.
Bournemouth should have been out of sight as Lewis Grabban's effort was cleared off the line by Jon Harley and Wes Fogden hit the post from an angle he really should have scored from.
And Paul Groves' side paid for their profligacy as Brian Howard scored a superb solo goal, dribbling the ball towards the box before switching to his left foot and curling the ball past a helpless Shwan Jalal.
Despite the equaliser, Bournemouth still should have come away with the win as both MacDonald and substitute Lee "Scummer" Barnard blazed over from yards out with the Portsmouth defence gaping.
The match somehow ended in a draw and went straight to penalties, which were taken in front of the Milton End.
Barnard was first up had his shot saved by Andersen much to the delight of the home fans. Howard, Liam Walker, Ashley Harris and Rodgers all clinically dispatched their spot kicks along with the other Bournemouth players who followed.
That was until Marc Pugh stepped up to take the Cherries' final spot kick, which sailed over the bar and sent Pompey into the second round of the competition.
Whilst the game was entertaining, the manner of Pompey's defending was extremely worrying given how many clear cut chances Bournemouth created. On another night we may well have been thrashed.
I was also slightly disappointed with Harris, who was never really in the game when given the chance to impress. Thompson will also need more time to gel with his back four after he was subbed at half-time.
On the positive side, Dumbuya continues to be a threat down the right, Rodgers was instrumental in our success once again whilst Williamson and Walker improved Pompey's overall passing when they come on.
Still, I feel there is much work to be done and the team must improve if Pompey are to win their first league game at Crawley on Sunday.