A stunning strike from Nick Awford sent Pompey Academy into the third round of the FA Youth Cup.
The scoreline was level at 1-1 when the midfielder strode forward in the 57th minute against Woking last night.
He then crashed a spectacular 30-yard shot which screamed into the net to get the majority of the 561 Fratton Park crowd on to their feet as Andy Awford’s side regained the lead.
By that stage, the visitors had been reduced to 10 men following skipper Isaac Nkosi’s second yellow card just after half-time.
The Cards had earlier fought back from Liam Triggs’ 30th-minute opener, the left-back netting following a mistake from keeper Liam Allen.
Yet Danny Taylor headed home on 43 minutes to ensure the match went in all square at half-time.
So it remained until Awford intervened with his magnificent drive from long distance which proved to be the decisive moment as they clinched a 2-1 success.
The Academy will now make the trip to Bolton in the third round as they seek to progress further in the competition.
Andy Awford was back in charge of the youngsters for the visit of the non-leaguers following his work with Guy Whittingham with the senior players.
And his side broke the deadlock in the 30th minute after a mistake from Woking keeper Allen.
Bradley Tarbuck delivered a corner from the left and when Allen dropped the ball, Triggs was on hand to force it over the line at the third time of asking.
Pompey received a setback in the 39th minute when left-winger Jack Maloney limped out of the action, replaced by Jae Heon Kim.
And moments later, Woking drew themselves level, Ndjeka delivering a superb ball from the right and Taylor getting ahead of Ben Close to plant a powerful header into the net.
Woking were reduced to 10 men within two minutes of the second half starting after Nkosi was dismissed.
The Cards skipper was given his second yellow card of the game following a foul on substitute Kim in a decision which appeared harsh.
It gave the hosts the initiative and, in the 57th minute, Awford moved forwards and crashed an unstoppable 30-yard effort past Allen.
That proved to be the piece of quality which settled the match as the Blues marched into the third round for a date with Bolton.
Pompey: Connor O’Hara, Ben Close, Josh Warren, Jack Whatmough,
Liam Triggs, Lewis Horsburgh,
Nick Awford, George Branford,
Jack Maloney (Jae Heon Kim 39), Bradley Tarbuck, James Hartson (Harry Medway 86). Subs not used: Nick Tarasenko, Chad Field,
Woking: Allen, T John (Young 78), Stone, Nkosi, Gatcum, Lobonza, Taylor (Curd 69), Findlay, Ndjeka, Manderson, Antwi (Dore 64). Subs not used: J John, Gibson.