The Netherlands were knocked out of the Nations League by Spain on penalties after coming back three times against the European Champions in a pulsating contest in Valencia.

Donyell Malen missed the decisive sudden-death spot-kick after both teams had converted four of their first five penalties, allowing Pedri to fire Spain into the semi-finals.

Malen had missed a glorious chance to win the tie in the last minute of extra-time when Kenneth Taylor found him in space on the right-hand side of the penalty area, but Malen’s shot lacked conviction and Unai Simon gathered the ball easily.

Earlier teenage sensation Lamine Yamal looked to have won the tie with a moment of magic in the first period of extra time, when he controlled a wide pass by Dean Huijsen with the outside of his left foot before curling a shot high past Bart Verbruggen from the edge of the penalty area.

But Oranje equalised for the third time in the 108th minute when Xavi Simons was brought down by Unai Simon when clear on goal for the third penalty of the match. The Spanish goalkeeper escaped with only a yellow card, but was unable to keep out Simons’ shot.

Disputed penalty

Having equalised in the last minute in the first leg in Rotterdam, Spain went ahead in the tie after just six minutes when Mikel Oyarzabal went down under the challenge of Jan Paul van Hecke.

Referee Clément Turpin pointed to the penalty spot, waving away the protestations of the Dutch players, and Oyarzabal got up to fire the ball into the top corner.

Oyazarbal had the ball in the net again minutes later from an offside position, while Oranje struggled to create any clear chances despite having the majority of possession.

Nico Williams and Yamal were a constant threat for Spain from the wing, with Williams twice drawing good saves from Bart Verbruggen.

Depay century

But early in the second half the Dutch were handed a lifeline when Turpin penalised Robin Le Normand for a push on Memphis Depay. The striker, playing in his 100th international match, dispatched the penalty himself for his 47th goal in an orange shirt.

Oyazarbal put Spain back in front in the 72nd minute after Williams dribbled to the edge of the area before passing to his unmarked team-mate, who headed into the net after Verbruggen had blocked his first attempt with his shoulder.

With 12 minutes to go and Spain seemingly cruising, Ronald Koeman threw on Noa Lang and Xavi Simons. The substitutions had an almost instant effect as Lang forged an opening on the left-hand side, cut back to Simons and the winger played in defender Ian Maatsen, who lashed the ball high into the net from a narrow angle.

Tijjani Reijnders and Depay had good chances saved by Simon as Oranje looked more threatening in the closing minutes, while Verbruggen again had to be alert to stop Williams as the clock ticked past 90 minutes.

Head coach Ronald Koeman said his team had shown over the two legs that they were capable of matching the best teams in Europe.

“We’ve shown again what we can and should expect of each other,” he told NOS. “We lost tonight on penalties, but we created a lot and we really had a go at Spain, and that’s a mentality that we need to take forward.”