Crouch the saviour for Pompey

Ragged Pompey surrendered a two-goal first-leg advantage inside 32 minutes as Guimaraes capitalised on sloppy defending to force extra-time. First Brazilian striker Douglas shot home in the 19th minute before Joao Alves added a second from 35 yards.

But Crouch made no mistake for his 100th goal in club football when nodding in at the far post from Glen Johnson's delivery in the 104th minute - and he then added an emphatic second from substitute Nadir Belhadj's pass.

The visitors paid the price for a sluggish start when Douglas drilled a shot into the net beyond David James in the 19th minute, with Portsmouth having made a mess of clearing a corner after Aguiar Rocha Danilo's header was deflected behind.

Distin and captain Sol Campbell both failed to cut out the ball to the Brazilian who found ample space in the area to fire it home.

Douglas was booked, presumably for over-celebrating his goal, but it was not long before the home fans had something else to cheer.

Miguel Flavio gave Pompey another scare with a long-range strike and there was a sense of the inevitable when they wiped out the visitors' advantage after 32 minutes when Joao Alves' 35-yard shot from a short free-kick fizzed past the unsighted David James.

In the second half, Portsmouth started to dominate possession, England right-back Johnson finding plenty of scope as a right-winger. But James had to make a save after 62 minutes when Douglas let fly from outside the area.

The vital away goal would not come for Pompey and they were made to pay for their first half sloppiness by having to go into extra time before finally finishing off their opponents.