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Swansea have been handed the difficult task of facing Italian giants Napoli in the last 32 of the Europa League, while Tottenham will face Ukrainian outfit Dnipro.
Swansea face a daunting task after being paired with Napoli, who are managed by former Liverpool and Chelsea boss Rafael Benitez and will be one of the favourites to win the tournament.
The Italians were in the same group as Arsenal in the Champions League but despite winning four of their six games, failed to qualify as the Gunners and Borussia Dortmund went through instead.
If Swansea can cause an upset and knock the Italians out, then they face a stern test in the last 16 against either Portuguese champions Porto or German side Eintracht Frankfurt.
Meanwhile, managerless Spurs must first of all get past former boss Juande Ramos, who was in charge at White Hart Lane for just under a year and will no doubt be out for revenge against the club who sacked him.
Spurs may have struggled for results in the Premier League under Andre Villas-Boas but they have been on top form in the Europa League with six wins out of six to top Group K.
Spurs will be expected to get through against Dnipro, and if that is the case they will face either Greek side PAOK or last season’s runners-up Benfica in the last 16.
In the other stand-out ties, Juventus will face Turkish outfit Trabzonspor, Valencia play Dynamo Kiev, while Real Betis take on Rubin Kazan