Chris Smalling sent England to Euro 2016 on the back of another win, but the late header could not mask an underwhelming display against Portugal.
The third and final preparation game was always likely to prove the toughest, but few expected a toothless and disjointed attack to be the main concern against the side eighth in the world.
England's defence had been the overriding concern ahead of the Wembley encounter, but Roy Hodgson's inability to effectively shoehorn the attacking triumvirate of Wayne Rooney, Harry Kane and Jamie Vardy into the same line-up was main issue in the 1-0 win against the 10 men of Portugal.
Smalling's late header was one of few moments for the sell-out Wembley crowd to shout about, with Vardy and Kane struggling to make an impact either side of Rooney as the Three Lions lacked attacking coherence and edge.
Even the first-half sending off of Bruno Alves for a horrific high challenge on Kane did little to help on a night punctuated by poor passes and choices.
The struggles of Vardy, Rooney and Kane will dominate much of the post-match conversation, but at least England head into the Group B opener against Russia on the back of a win courtesy of Smalling's first international goal.
It was an exciting end to a match that started slowly and continued in a similar vein.
Kane created the first chance of note after 11 minutes, only for a point-blank Rui Patricio save to deny a Rooney shot that would have been ruled out for offside anyway.
That was one of few moments of note in a tepid first half and at the other end James Milner was fortunate to send a wayward pass to Nani, with the unsurprisingly greedy attacker blazing well over from distance.
Danny Rose produced a timely challenge to stop a whipped Eliseu cross finding its intended target and Ricardo Carvalho headed over from a corner as Portugal looked to capitalise on England's disjointed display, epitomised by striker Kane's short corner straight to an opponent.
Rooney saw a header denied at the back post after a deep cross from man-of-the-match Kyle Walker, who came close to opening his account in style as a first-time strike flew inches wide.
The goal would not have disguised a difficult first-half display for England, though, and Hodgson was robbed of a chance to try to solve their attacking issues in the 36th minute.
Kane appeared little threat when challenging for the ball wide on the right, yet defender Alves inexplicably flew in with a head-high challenge that led referee Marco Guida to brandish a red card.
It was deserved punishment for a ridiculous challenge that all-but killed the match as a meaningful test, with Kane forcing Patricio into a save as Portugal attempted to regroup.
When they re-emerged for the second period the visitors had shored things up at the back and England were struggling find a way through the lines.
It took a 30-yard effort from Eric Dier to call the Portugal goalkeeper into action after the break, although it began a spell of pressure from the hosts.
Walker continued to look one of England's most dangerous players and was caught just outside the box by Andre Gomes, with Gary Cahill's header from the resulting free-kick blocked by Jose Fonte.
Kane saw a free-kick deflected wide from distance and substitute Daniel Sturridge hit a snap-shot across goal as England pushed for a winner, which arrived four minutes from time.
Substitute Raheem Sterling superbly bent in a right-footed cross and Smalling darted in to direct a header past Patricio, belatedly giving the home fans something to cheer on a frustrating night.
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