BELGRADE (Reuters) - Former European Cup winners Red Star Belgrade were held to a 1-1 home draw by Moldovan side Sheriff Tiraspol on Tuesday in the first leg of their Champions League third qualifying round tie after they were reduced to 10 men.
PSV Eindhoven, the 1988 winners, closed in on the playoff round with a 3-0 home rout of Danish side Midtjylland and 2004 runners-up Monaco won 2-0 at Sparta Prague.
A last-gasp goal by Steven Davis kept Scottish champions Rangers in contention to advance although they suffered a 2-1 reverse at Swedish side Malmo, who took a two-goal lead through Soren Rieks and Serbian striker Veljko Birmancevic.
Sheriff took the lead out of the blue in Belgrade as Frank Castaneda curled in a sublime free kick before Frenchman Lois Diony equalised on the stroke of halftime after he took advantage of some poor defending.
Both sides missed several chances to snatch a winner after Red Star, who won Europe's premier club competition in 1991, had midfielder Guelor Kanga sent off in the 57th minute for a second yellow card.
"Sheriff are a team full of speed and talent," Red Star coach Dejan Stankovic told Arenasport television after a frustrating evening for the Serbian champions.
"Having fallen behind, we managed to equalise and create some chances after we were reduced to 10 men. It’s not over yet, we can pull it off in the return leg."
With the away goals rule no longer in effect, Stankovic will rely on his misfiring side to show more bite in Moldavia after creating few chances against a rugged Sheriff defence.
An impressive first half saw PSV take a 19th-minute lead against Midtjylland as 19-year-old English prospect Non Made unleashed a superb shot from 20 metres into the top corner.
Germany midfielder Mario Goethe made it 2-0 in the 29th with a heavily deflected shot and Cody Gakpo added the third three minutes later with a simple tap-in from two metres after a flowing move.
A dominant Monaco forced Sparta into submission as midfielder Aurelia Tchouameni gave them the lead with a thumping header before Kevin Holland drilled a powerful shot into the roof of the net.
Rangers were rattled by two quickfire goals as Birmancevic set up the opener for Rieks in the 47th minute and then rifled in a sumptuous volley two minutes later before Davis kept Rangers' hopes alive with the last kick of the game.
Elsewhere, Shakhtar Donetsk came from behind to earn a 2-1 win at Belgian side Genk and a stoppage-time goal from Vincent Sierro gave Young Boys a 1-1 draw at Romanians Cluj who took a third-minute lead through Cristian Manea.
Olympiakos Piraeus also left themselves with work to do following a 1-1 home draw with Bulgaria's Ludogorets Razgrad.
On Wednesday, Spartak Moscow host twice winners Benfica, Dinamo Zagreb are at home to Legia Warsaw and Hungarians Ferencvaros entertain Slavia Prague.
(Writing by Zoran Milosavljevic; Editing by Toby Davis)