Just when Portsmouth’s first foray into senior European football seemed likely to be cut short almost before it had begun, Peter Crouch came to their rescue last night with the two extra-time goals that booked their passage into the Uefa Cup group stage, including the 100th goal of his club career.

With Portsmouth having seen their 2-0 first-leg lead wiped out and with a penalty shoot-out looming, Crouch headed in Glen Johnson’s right-wing cross from point-blank range and settled any remaining nerves with a ferocious shot into the top corner.

“We let ourselves down in the first half, we weren’t good enough, but in the second half we came out and dominated,” Crouch said. “I think our fitness told in the end. It was a fantastic cross from Glen and made the first goal an easy one.”

Guimarães is the birthplace of the Portuguese nation, so there should have been no better stage for Portsmouth to make some history of their own. Harry Redknapp’s team had what looked a straightforward job if they were to reach the group stage, but it did not work out as planned and a jittery and uncertain defensive display allowed the Portuguese side to level the tie before the interval.

The late kick-off time gave the 2,700 Portsmouth supporters who had made the trip plenty of time to soak up the sunshine and the local wine, and with three hours to go, the Largo Do Toural, a square about half a mile from the stadium, was packed with fans of both teams enjoying what resembled a 500-a-side game of head tennis.

When they arrived at the handsome Estádio Don Afonso Henriques, they discovered that Redknapp had switched to a 3-5-2 formation, bringing back Sean Davis — after he had missed two matches with a groin injury — to provide extra midfield cover in front of Sol Campbell. It was a controversial move — the system had brought a 3-0 victory away to Everton when it was first used, but was so unsuccessful on its next two outings that it was abandoned after 45 minutes on each occasion.

Redknapp’s decision would have been vindicated if Portsmouth had got an early goal, but when Jermain Defoe pilfered the ball from Gregory, the central defender, Danilo got across smartly to intercept a pass intended for Crouch.

Instead it was Guimarães who took the lead after 19 minutes through Douglas, the Brazilian striker who had missed the first leg because of injury.

David James came for a corner from the right and missed it completely, but breathed again when Danilo’s shot hit a defender and went for another corner. However, it was only a temporary reprieve. The second kick was half-cleared but when Luciano, the left back, returned the ball into the penalty area, it skidded off Campbell’s head as he and Sylvain Distin got in each other’s way, allowing Douglas to beat James with ease.

It got worse as Guimarães levelled the tie after 32 minutes. João Alves, the Portugal midfield player, collected a short free kick 35 yards out and hit what should have been a hopeful but doomed low shot. James, though, may have been unsighted by Douglas, who jumped over the ball at the last second, and it sped past him as he stood immobile.

An away goal would have turned the tide back in Portsmouth’s favour and Johnson came close to providing it in the final minute of the first half. He cut inside and shot hard and true with his left foot, but Nilson threw himself low to his right to turn the ball away for a corner.

As Portsmouth went forward in the second half, Defoe put Armand Traoré in on goal, but his first touch was too heavy and Nilson was able to claim the ball. Then Crouch volleyed tamely at the goalkeeper when he might have pulled the ball back to the unmarked Defoe.

Johnson was beating Luciano almost at will and Defoe was his usual persistent self, but the openings refused to come and although Guimarães were reduced to long shots that James now dealt with comfortably, extra time looked inevitable, especially when Crouch jumped to meet Traoré’s cross only to nod the ball into Nilson’s hands. Crouch, though, was to have the final word to make a late night for Portsmouth’s supporters a worthwhile one.

Vitória Guimarães (4-1-2-3): Nilson — Andrézinho, Danilo, A Gregory, Luciano (sub: Fajardo, 79min) — João Alves, Flávio, Wenio — Y Desmarets, Douglas, Roberto (sub: Carlitos, 62; sub: J Coral, 75). Substitutes not used: Serginho, Moreno, Tiago, Momha. Booked: Flávio, Danilo.

Portsmouth (3-5-2): D James — N Pamarot, S Distin, S Campbell — G Johnson, R Hughes (sub: N Belhadj, 99), S Davis (sub: A Mvuemba, 73), L Diarra, A Traoré — J Defoe (sub: Y Kaboul, 101), P Crouch. Substitutes not used: J Ashdown, H Hreidarsson, Kanu, G Little. Booked: Johnson.

Referee: Selçuk Dereli (Turkey).