Pompey stormed into the second round of the Johnstone’s Paint Trophy southern section with a magnificent 3-1 victory at Yeovil Town.
The Blues produced a stirring second-half display to blow their League One opponents away.
And the hosts had little answer to a ruthless display of finishing from Andy Awford’s men.
Pompey made six changes to the side that lost 1-0 to Newport County in League Two on Saturday as Alex Wynter, Johnny Ertl, Dan Butler, Nick Awford, Nigel Atangana and Miles Storey all returned to action.
After a largely uneventful first-half, Jed Wallace put the visitors ahead on 55 minutes at Huish Park when he finished a sweeping Blues move after exchanging passes with Craig Westcarr inside the Glovers box.
And it was that man Wallace again who latched on to Wynter’s incisive through-ball to double the visitors’ advantage on 73 minutes.
Two minutes later, Westcarr put the game beyond doubt when he collected Storey’s slide-rule pass to coolly lob the ball over helpless home keeper Chris Weale to send the 692-strong travelling support into raptures.
The hosts pulled a goal back with six minutes left on the clock when Nathan Ralph blasted home off the underside of the crossbar.
But by then it was too little too late as Awford’s side deservedly advanced to the second round.
The only minor concern for the Blues on a memorable night was the enforced withdrawal of Atangana just before the half-time interval.