A single goal from Dario Silva on 36 minutes was enough to give Portsmouth victory over Ipswich in the FA Cup.
Gavin Williams had missed a gilt-edged chance for Town before Pompey took the lead against the run of play when Silva headed home Matt Taylor's cross.
Ipswich came close to equalising after the break when Danny Haynes saw his low drive across goal shave the post.
And Blues defender Jason De Vos saw his near-post header hit the post as the hosts failed to make the breakthrough.
Pompey's new co-owner Alexandre Gaydamak decided against attending the match at Portman Road, having tied up his investment deal on Friday.
And travelling Pompey fans were not able to watch their two new recruits - strikers Emmanuel Olisa and Benjani Mwaruwari - with both players still waiting on international clearance.
Darren Currie carved out Town's first opening on eight minutes when he drove his 25-yard effort over the bar, and minutes later Ian Westlake followed suit from a similar range.
Ipswich were controlling large parts of the game without exerting their dominance, yet they should have made their possession count before the half-hour mark when Williams missed a clear opportunity from 10 yards.
Scott Barron sent a dangerous centre into the box only for Pompey's Gregory Vignal to stick out a leg with Haynes in close proximity, but the clearance fell kindly to the Williams, who could only fire the ball wide.
Against the run of play, Portsmouth took the lead on 36 minutes when a surging run and cross down the left-hand side by Matt Taylor was met at the back post by the unmarked Silva.
Minutes later Lomana LuaLua twisted and turned his marker on the edge of the box but his right-foot curling effort went inches past the post.
After the break, LuaLua burst into the box only for Fabian Wilnis to dispossess him as he closed in on goal.
Blues teenager Haynes almost equalised on the hour mark but his low right-foot effort from just inside the box shaved the far post.
And Town went closer still when defender De Vos saw his near post header from Currie's free-kick hit the post and cleared to safety.
Ipswich were continuing to have the lion's share of play while Portsmouth were limited to sporadic forays into the opposition's half.
Although Pompey never really threatened to add to their advantage, at the other end Town lacked a killer edge in front of goal which could have troubled their Premiership opponents.
Ipswich: Supple, Wilnis, Naylor, De Vos, Barron, Magilton (Sito 56), Westlake (Juan 81), Richards (Garvan 56), Williams, Haynes, Currie.
Subs Not Used: Price, Horlock.
Portsmouth: Westerveld, Priske, Stefanovic, O'Brien, Vignal, O'Neil, Hughes, Diao, Taylor, LuaLua (Karadas 89), Silva (Todorov 68).
Subs Not Used: Guatelli, Cisse, Songo'o.
Booked: Priske, Silva.
Goals: Silva 37.
Ref: D Gallagher (Oxfordshire).