The Portuguese paid the price for another poor first half display, with a spirited second half effort not enough to avoid a damaging defeat, which leaves Jose Couceiro’s men with just one point from two games.

Manuel da Costa: “We only started to play after we were losing 2-0.”

Coach Couceiro made three changes, with Antunes and Amoreirinha replacing Jose Goncalves and Felipe Oliveira in the full-back positions. Meanwhile, Yannick Djalo was sacrificed in order to bring in Belenenses midfielder Ruben Amorim.

A frantic first ten minutes saw the Dutch looking the most likely to score an early goal, with Amoreirinha struggling to contain rampaging left-sided player Royston Drenthe, leading to the new Cluj signing picking up an early booking.

Drenthe causes panic

Drenthe created the first noticeable chances of the match, first escaping the attentions of Amoreirinho to find Bakkal in the centre, but the midfielder sent the ball over the crossbar. Then, the tricky wide man raced to the byline and cut the ball back for Julian Jenner to miss the target.

The hosts took the lead just after the hour mark from the penalty spot, after Portugal goalkeeper Paulo Ribeiro brought down Rigters inside the box, although the forward was certainly looking for the decision. Ryan Babel stepped up to calmly sent Ribeiro the wrong way to give his side the lead.

Portugal struggled to create much in the way of opportunities, with Nani again ineffective on the flanks. A decent passage of football saw Joao Moutinho break down the right and stand a cross up to the back post for Hugo Almeida to tamely head wide.

Holland almost increased their lead before the break when Rigters latched onto a pass and slid the ball past Ribeiro onto the inside of the post, with Manuel da Costa doing brilliantly to deny Jenner scoring from the rebound.

Pereira impresses

With Amoreirinha struggling and on a yellow card, Couceiro brought on Portugal’s fifth full-back of the tournament in Joao Pereira at the interval. The Gil Vicente man acquitted himself well in the second half, with several runs down the right causing the Dutch problems.

Just short of the hour mark, in what was an improving Portuguese performance, Pereira burst infield and found Nani on the left of the area. The new Manchester United signing laid the ball off to Almeida, who struck a sweet first time effort with his left foot to force Vermeer into a save.

Manuel Fernandes and Almeida both had long-range shots clear the crossbar and Jose Semedo made space in the area to shoot straight at Vermeer, as Portugal began to exert increasing pressure on their opponents.

However, when it appeared that Portugal might have been close to an equaliser, they conceded again. More superb set-up play from Drenthe saw him jink to the byline and cut the ball across goal, where Rigters was more alert than da Costa and stabbed in from close range.

Veloso stunner

Despite the seemingly fatal setback, Portugal pulled a goal back almost immediately. Sporting midfielder Miguel Veloso curled home and outstanding 25-metre free-kick, which is probably the goal of the tournament so far.

There was no equaliser though, despite the late introduction of Djalo, and Couceiro’s side face an uphill task to avoid going home early. Portugal must beat Israel in Saturday’s final group game, while also relying on the already qualified Dutch to beat Belgium.

PortuGOAL man of the match: Joao Pereira
The ex-Benfica full-back invigorated Portugal in the second half with a series of purposeful runs and dangerous attacking raids

Holland:
Waterman (Vermeer, 34), Zuiverloon, Vlaar, Donk, Jong-a-Pin (Pieters, 78), Maduro, Drenthe, Babel, Bakkal, Rigters, Jenner (Beerens, 45)
Yellow Cards: Jong-a-Pin (61), Drenthe (89)

Portugal:
Ribeiro, Amoreirinha (Pereira, 45), Antunes, Semedo, da Costa, Veloso, Amorim (Varela, 57), Fernandes (Djalo, 81), Moutinho, Nani, Almeida
Yellow Cards: Amoreirinha (4), Veloso (88), Pereira (93)

Goals:
[1-0] Babel, 33
[2-0] Rigters, 75
[2-1] Veloso, 77