Tottenham have it all to do at home in the Europa League's round of 32 after Ukranian opponents FC Dnipro earned a 1-0 win against the London side.
Dnipro - now managed by former Tottenham boss Juande Ramos - were able to convert a 35th minute penalty to gain the upped hand in the tie.
Ukrainian international Yevhen Konoplyanka proved to be a thorn in Tottenham's side for the majority of the game.
The winger, who was targeted by Liverpool in the January transfer window, scored the match's decisive goal from the penalty spot after a foul by Jan Vertonghen.
Tim Sherwood's side may have walked away from Ukraine with something from the match, had Roberto Soldado not blazed his shot over the bar from five-yards out.
Meanwhile, Swansea were held to a goalless draw at home to Italians Napoli. The Welsh side were perceived as outsiders for this match at the Liberty Stadium against top-four chasing Napoli.
Yet it was the home side who were dominant throughout, only denied by fine performances from two goalkeepers.
First it was Rafael Cabral who kept out efforts from Wayne Routledge and Angel Rangel. The Brazilian keeper picked up and injury and was replaced by Pepe Reina in the second half. The Spaniard picked up where Cabral left off, denying Routledge and Ashley Williams.
Elsewhere, Italian giants Juventus had no problem dealing with Turkish opponents Trazbonspor, with a late strike from Paul Pogba following Southampton loanee Pablo Osvaldo's 15th minute opener.
Fellow Serie A side Fiorentina also eased through their match with Danish opponents Esbjerg. Alessandro Matri opened the scoring for the away side, but they were pegged back two minutes later by Martin Pusic.
Josp Ilicic put Fiorentina back in front, before former Liverpool midfielder Alberto Aquilani put the match beyond doubt from the penalty spot.
Dutch champions Ajax were stunned at home Red Bull Salzburg, as an outrageous halfway line-lob from Jonathan Soriano helped the Austrians seal victory and a major advantage in the tie.
Lazio also suffered a shock loss in Rome to Bulgarian outfit Ludogorets Razgrad. A solitary effort from Roma Bezjak just before half time proved enough in a match marred by red cards for both sides.
Porto were denied victory in their clash against Eintracht Frankfurt due to a comedy own goal from full-back Alex Sandro. The Portuguese side were 2-1 up courtesy of goals from Ricardo Quaresma and Varela before the Brazilian hit the back of his own net.
Anzhi Makhachkala 0-0 KRC Genk
Dynamo Kiev 0-2 Valencia CF
Esbjerg fB 1-3 Fiorentina
FC Chornomorets Odesa 0-0 Lyon
FC Dnipro 1-0 Tottenham
Juventus 2-0 Trabzonspor
PAOK Salonika 0-1 Benfica
Slovan Liberec 0-1 AZ Alkmaar
Ajax 0-3 FC Red Bull Salzburg
FC Porto 2-2 Eintracht Frankfurt
Lazio 0-1 Ludogorets Razgrad
Maccabi Tel Aviv 0-0 Basel
NK Maribor 2-2 Sevilla
Real Betis 1-1 Rubin Kazan
Swansea 0-0 Napoli
Viktoria Plzen 1-1 Shakhtar Donetsk
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