Dynamo Kiev, who left out former European Footballer of the Year Andriy Shevchenko, slumped to a 2-0 home defeat against Rubin Kazan in a Champions League third qualifying round, first-leg tie on Tuesday.
Elsewhere, 1966 European Cup runners-up Partizan Belgrade lost 2-1 at Belgian league champions Racing Genk, while Dutch side Twente Enschede eased past Romania’s Vaslui 2-0 thanks to a double from Austria striker Marc Janko.
The third qualifying round winners are battling for a spot in the playoff matches, where they could seal a berth in the competition proper.
In Ukraine, Alan Kasaev struck from close range in the sixth minute to give Rubin the lead, before Bebras Natcho added a second goal for the Russian side with a 68th-minute penalty.
Shevchenko was left sitting on the bench as an unused substitute, while Dynamo failed to capitalize on a host of scoring chances. Coach Yuri Semin’s team will now have a mountain to climb in next week’s return match.
The two teams also met in the Champions League group stages two seasons ago, Dynamo winning in Kiev 3-1 before holding Rubin to a 0-0 draw in Kazan.
In Scotland, Rangers’ hopes of making the Champions League group stages hang by a thread after Malmo claimed a deserved 1-0 win at Ibrox in the first leg of their third qualifying round match on Tuesday.
The Swedes, who are halfway through their season, started the match far sharper than the Scottish champions and secured a vital away goal through a wonder striker from Daniel Larsson in the 16th minute.
Malmo continued to have the better chances, with Brazilian Wilton Figueiredo causing several panics in the Rangers defense.
In Belgium, Genk came from behind to earn a 2-1 home win over Serbian opponents Partizan thanks to a superb stoppage-time goal from late substitute Marvin Ogunjimi.
The striker, who came on in the 85th minute, sent a vociferous home crowd into raptures when he controlled a deep, searching pass and beat goalkeeper Vladimir Stojkovic with a delightful lob from 10m out.
Genk defender Calvin Anele Ngcongca was sent off for violent conduct in the 32nd minute, but Partizan also had forward Stefan Babovic dismissed shortly after the interval for two bookable offenses.
Nemanja Tomic had put Partizan in front, but the same player also gave away a soft penalty five minutes later that was converted by Jelle Vossen in the 70th minute.
In Enschede, two-goal Janko led Twente to victory over Vaslui in a match played at the Gelredome in Arnhem.
Twente were unable to use their home ground after a roof collapsed at the stadium earlier this month, resulting in the death of two -construction workers.
Janko converted a penalty after 34 minutes, before adding a second goal after the break.
In other matches, Lithuania’s Ekranas Panevezys drew 0-0 at home to BATE Borisov of Belarus, while Zestafoni were held to a 1-1 draw in Georgia by Sturm Graz of Austria.
Slovakia’s Slovan Bratislava drew 0-0 in Cyprus against APOEL Nicosia and Polish side Wisla Krakow triumphed 2-1 at Litex Lovech of Bulgaria.
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