Adam McGurk was the two-goal hero as Pompey ended their FA Cup hoodoo today.
The Blues won in the competition at the eighth time of asking as they picked up a 2-1 over Macclesfield.
McGurk got both goals in the first half in front of a crowd of 9,834 at Fratton Park.
In between those efforts a mistake from Brian Murphy gave the Silkmen hope as he cannoned a clearance into Kristian Dennis and the ball ended up in the net.
There was a first glimpse of new striker Marc McNulty as Pompey advanced without firing on all cylinders.
It took just three minutes for Pompey to take the lead with the game’s first attack.
It was a lovely pass from Kyle Bennett which put McGurk in, and the attacker scooped his shot over Shwan Jalal.
That put Pompey in control but the visitors were level after 15 minutes following a gaffe from Brian Murphy.
There appeared little danger as Enda Stevens went back to the Irishman from a throw, but he cannoned his clearance of Kristian Dennis who knew little about it as the ball flew into the net.
Pompey nearly replied immediately but Jalal saved Gareth Evans’ angled drive.
Murphy then pulled off a decent stop to deny Danny Whitehead from 25 yards.
Evans then saw his shot cleared off the line by David Fitzpatrick before Pompey equalised in first-half stoppage time from that man McGurk.
It was Stevens who fired a ball into the box, and after a series of ricochets, the ball was slotted home by McGurk.
Murphy had to be sharp to deny Danny Whittaker’s effort two minutes after the restart.
Dennis then fired over eight minutes later after Stevens’ clearance cannoned off Doyle.
McNulty’s introduction lifted a flat crowd with 66 minutes played.
He showed some brightness and a good turn of pace, but should have done better when heading over Evans’ cross with seven minutes left.
Another late chance showed his power as he hammered a drive which Jalal pushed away.
There was a late let-off for Pompey as Danny Whittaker fired over when well placed in space 12 yards out.
But the Blues held on comfortably to progress to the second round.