Cristiano Ronaldo scored his 700th career goal on Monday but could not prevent Portugal slipping to a 2-1 defeat to Ukraine in UEFA 2020 European Championship qualifying:
The win means Ukraine move eight points clear at the top of Group B and secure qualification to Euro 2020, while reigning European champions Portugal still have work to do to reach the finals.
Roman Yaremchuk fired the hosts into the lead after just six minutes. Portugal goalkeeper Rui Patricio could only parry a header from Serhiy Kryvtsov, allowing Yaremchuk to pounce on the loose ball and prod home.
Ukraine doubled their lead through Andriy Yarmolenko on 27 minutes. Vitaliy Mykolenko surged down the left and sent in an early ball for the West Ham United man to sweep home.
Portugal pulled one back from the penalty spot on 72 minutes after Taras Stepanenko blocked a shot with his arm and was sent off for a second bookable offence.
Ronaldo smashed home the spot-kick to hit the latest landmark in his glittering career but could not inspire a comeback as Portugal stay second in Group B.
Ukraine were the dominant side in the first half and were good value for their two-goal lead at half-time.
Portugal failed to deal with an early corner, allowing Krivtsov to direct a firm header goalwards. Patricio managed to block the shot but only as far as Yaremchuk who made no mistake from close range.
The hosts then carved Portugal open for their second goal. Mykolenko did well down the left and was given time to pick out Yarmalenko to slot a neat finish past Patricio, as shown by Sky Sports Football (UK only):
Ronaldo looked Portugal's most likely goalscorer in the first half but had few sights of goal. The Juventus forward's best effort was a shot that was tipped over the bar by goalkeeper Andriy Pyatov.
Portugal's captain twice tested Pyatov early in the second half. He fired a free-kick straight at the goalkeeper on 50 minutes and forced the 35-year-old into a diving save with a stinging shot just before the hour.
Manager Fernando Santos sent on Atletico Madrid striker Joao Felix for Bruno Fernandes for the final 30 minutes as he sought a way back into the tie.
Portugal were offered a lifeline on 72 minutes when they were awarded a penalty. Stepanenko was adjudged to have blocked Bruma's shot with his arm and picked up his second yellow card to leave the hosts with 10 men.
Ronaldo smashed home the penalty for his 700th goal as a professional footballer:
Portugal pressed for an equaliser in the closing stages and came close with two efforts in stoppage time that caused chaos in the Ukraine penalty area.
Ronaldo forced Pyatov into yet another save with a powerful header. The ball then fell to Pep at the far post but his effort was blocked on the goalline.
Danilo then hit the crossbar with a terrific shot from range that beat Pyatov and dropped into the penalty area before being scrambled away as Ukraine held on to clinch top spot in Group B.
Ukraine's next fixture is a friendly against Estonia on November 14. Portugal take on Lithuania on the same day in qualifying. The two nations then play their final Group B fixtures three days later. Ukraine are away at Serbia, while Portugal head to Luxembourg.