Past winners lead pursuit in last 16

Six former winners of the UEFA Cup are waiting to resume their pursuit of the trophy when the UEFA Europa League round of 16 begins on Thursday – and two of them will be in direct confrontation.

PFC CSKA Moskva welcome FC Porto to the Luzhniki Stadion for an encounter between two recent holders of the UEFA Cup, CSKA having triumphed in 2005 and Porto two years earlier. The hosts are unbeaten in the competition although they will have to improve on past results against the runaway Portuguese Liga leaders – no win in four and not a single goal scored – to retain hope of progress.

Liverpool FC have also yet to lose but the three-time UEFA Cup winners face a potentially tricky visit to SC Braga, who have achieved five victories in six European home fixtures this term – including against two British visitors, Celtic FC and Arsenal FC, in the UEFA Champions League.

Manchester City FC, meanwhile, have a first expedition to Ukraine to take on an FC Dynamo Kyiv team who put eight goals past Beşiktaş JK in the last round. Dynamo's Andriy Shevchenko once netted in a 6-0 rout of Manchester City with former club Chelsea FC; a repeat is unlikely yet City forward David Silva, a scorer at the Valeriy Lobanovskiy Stadium for Valencia CF, sees a tough evening in prospect. "They are a strong team that's hard to beat, especially at home," said Silva.

UEFA Cup winners in 1988, Bayer 04 Leverkusen are the competition's third and final unbeaten side but will have to be at their best to maintain that run at home to Villarreal CF, conquerors of SSC Napoli in the last 32. Villarreal striker Giuseppe Rossi predicts an "exciting and tough" contest, and it will not be the only one.

After a creditable UEFA Champions League debut campaign, FC Twente ousted FC Rubin Kazan in the round of 32 and must now tackle another Russian outfit in FC Zenit St Petersburg, who lifted the UEFA Cup in 2008 and were the only team to win all six group games.

This is one of two Russo-Dutch encounters taking place in the Netherlands on Thursday, with AFC Ajax, the 1992 UEFA Cup winners, entertaining FC Spartak Moskva. Ajax coach Frank de Boer and his assistant Danny Blind will want to fare better than when they faced Spartak in the competition as players with the Dutch club – losing home and away in the 1997/98 quarter-finals.

Another Eredivisie contender, PSV Eindhoven, have their own wrong to right as they seek a first-ever win against Scottish opposition when they host Rangers FC. Rangers have won three of the pair's four previous meetings yet may find it more difficult this time against rivals whose nine-game unbeaten sequence in the UEFA Europa League stretches back to August.

The same goes for Paris Saint-Germain FC, who ousted FC BATE Borisov on away goals last time out. The Parisians' next test is against an SL Benfica side who have just established a record for consecutive victories in domestic competition. If Benfica can transfer that form to Europe, PSG really will have their work cut out.