Pompey beat Basingstoke 5-4 on penalties to book their place in the third round of the Hampshire Cup.
Neither keeper had too much to do in a mostly uneventful contest, although both sides had late chances to win inside the 90 minutes.
Alex Bass saved two of the home side’s spot-kicks – and also missed one himself – to seal progress for the Blues.
Danny Cowley fielded a selection of first team players at The Winklebury Stadium, with Paul Downing skippering the side.
There were also outings for Bass, Connor Ogilvie, Michael Jacobs and Gassan Ahadme to complement the academy hopefuls.
Clear-cut chances were at a premium during the first half, although the visitors showcased some neat passing play at times.
Jacobs lined up a couple of free-kicks, but one slammed into the wall and another was claimed by keeper Paul Strudley.
Downing also met a corner from Alfie Bridgman with a back-heel that flew not too far wide of the post.
There were 37 minutes on the clock before either side realistically looked capable of breaking the deadlock, however.
And it was the home side that finished the half on top, with Ben Cook stealing possession and finding Aiden Lewis, who angled a shot narrowly wide.
A corner also caused problems, but a foul on Bass ensured the danger passed and the sides could go in level at the break.
Half Time: Basingstoke 0 Pompey 0
Basingstoke came close to scoring early in the second half, but Bass was equal to the strike from McKoy Palmer.
The danger was not over, though, and Ogilvie did well to prevent Lloyd Snell from tucking away the loose ball.
Pompey, meanwhile, were enjoying plenty of possession, but struggling to get through a well organised Dragons defence.
Jacobs won a free-kick in a dangerous position and, just like in the first half, his strike could not find a way through the wall.
The midfielder then tried his luck again and this time his shot took a deflection off team-mate Gassan and flew just past the post.
And the Blues came so close to scoring on 70 minutes, only for Dan Gifford’s strike to be superbly saved by Strudley.
The tie started to drift in the closing stages, but Ogilvie had a great chance to grab a late winner for Pompey.
He raced through unmarked to meet a corner from Jacobs, although could not keep his shot down and the ball ballooned over.
But Basingstoke had a late opportunity of their own, as D’Andre Brown took a neat touch on the edge of the box and hit a fierce effort just wide.
Full Time: Basingstoke 0 Pompey 0
Gassan, Jacobs, Gifford and Harry Jewitt-White all scored from the spot, but Downing’s effort was saved to sent the shoot-out into sudden death.
Bass stepped up, but was denied by Strudley, only for Daryl Wollers to waste his opportunity to win the tie for Basingstoke by blazing over.
Harvey Hughes then put the visitors back in control and Bass – who had already made one stop – ended the contest by denying Aiden Lewis.
Basingstoke (4-4-2): Strudley; Williams, Armsworth, Wollers, Haworth (Everiss 75); Snell (Lynch 66), Brown, Lewis, Palmer; Wilson (Reid 71), Cook (c)
Booked: Lewis
Subs not used: Mumford, Halliday
Pompey (4-1-4-1): Bass; Kaba, Downing (c), Ogilvie, Hughes; Jewitt-White; Gifford, Payce, Bridgman (Setters 68), Jacobs; Gassan
Subs not used: Steward, Spurway, Simpson, Howell
Referee: Sam Ogles
Attendance: 914