Porto are within reach of a Europa League quarter-finals berth with a 1-0 win at CSKA Moscow, while Spartak Moscow stunned Ajax.
Colombian midfielder Fredy Guarin was on hand to nab an invaluable away goal for Porto, cutting inside at the edge of the area and firing a well-directed effort beyond CSKA goalkeeper Igor Akinfeev in the 70th minute.
The result was just reward for the Portuguese club, who dominated the opening leg of their last-16 tie in freezing conditions at the Luzhniki Stadium.
Porto will take a handy aggregate into their home leg next Thursday, where – if their intimidating Liga Sagres form this season is any indication – they will prove very difficult to defeat.
Elsewhere, Spartak Moscow were surprise 1-0 winners at Eredivisie runners-up Ajax, with Brazilian midfielder Alex finding the net in the 57th minute.
The former Internacional playmaker took possession on the right flank and worked his way inside two Ajax defenders before dipping a left-footed shot into the top-left corner.
Ajax were unable to find a reply despite a spirited showing in the final half hour, and face an uphill battle to secure their passage to the last eight when they travel to the Russian capital next Thursday.
Fellow Russian club Zenit St Petersburg face their own struggle in next week’s home leg after they fell 3-0 at Dutch club Twente.
Netherlands international Luuk de Jong scored a brace either side of veteran midfielder Denny Landzaat’s 56th-minute goal, leaving Twente well-placed for a trip to the quarter-finals.
Paris Saint-Germain’s tie with Benfica is evenly poised after the French club fell 2-1 in Lisbon.
Congolese attacker Peguy Luyindula nabbed a valuable away goal in the 15th minute, but Maximiliano Pereira levelled in the shadows of half-time and Franco Jara saved Benfica’s blushes with an 82nd-minute winner.
Spanish side Villarreal can thank Nilmar for their surprise 3-2 win at Bayer Leverkusen, with the Brazilian ace netting an injury-time winner to put Villarreal in a strong position ahead of their home tie.
Michal Kadlec had opened the scoring for Bayer after the half hour, before strike duo Giuseppe Rossi and Nilmar put Villarreal up 2-1 by the 70th minute.
Gonzalo Castro looked to have secured a draw for the hosts two minutes later, but Nilmar struck again to bag a brace and keep Villarreal in the hunt for the quarter-finals.
Elsewhere, Scottish side Rangers held Dutch club PSV Eindhoven to a 0-0 draw in the Netherlands, Liverpool fell 1-0 at Sporting Braga and Dynamo Kiev defeated Manchester City 2-0.
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