Walter Smith's Scottish outfit experienced an epic journey which saw them play 18 European games to reach Manchester, only for them to fall at the final hurdle at the hands of the Russian champions.

Goals from Igor Denisov and Konstantin Zyrianov proved to be the difference between the two sides, with Dick Advocaat triumphing over his former club who had hoped to claim an historic quadruple this season but must now focus on completing a domestic treble.

Rangers were forced to soak up the pressure early on when Zenit's star man Andrei Arshavin was released through on goal, only to pull his shot wide of the upright and ripple the side-netting.

At the other end, Darcheville delivered a promising ball from the left with Barry Ferguson bearing down on goal, but the skipper was denied the opener by a timely Russian challenge.

Thomson then gave away a foolish free-kick 35 yards out. Radek Sirl took responsibility for the set-piece but Rangers goalkeeper Neil Alexander did well to smother after the ball had taken a wicked deflection en route to goal.

Alexander was called into action again when Hemdani lost possession just outside the box and the ball broke to Aleksandr Anyukov whose smart shot was initially fumbled and then held by the Gers keeper.

With Rangers doing little to trouble Vyacheslav Malafeev in the Zenit goal, the Russians were doing all the pressing and Zyrianov screwed wide of the near post after being set up for the shot by Roman Shirokov.

Steven Whittaker's header over the crossbar from Davis' cross failed to worry the Zenit goalkeeper before Darcheville was tripped by Denisov and Rangers were awarded a free-kick on the edge of the area.

It was a decent chance but Thomson's effort failed to make it past a wall of white jerseys after a tense build-up to the shot.

Kirk Broadfoot then appeared to handle in the box from an Arshavin cross seconds before the half-time whistle but no penalty was forthcoming from Swedish referee Peter Frojdfeldt and the first half ended goalless.

Rangers had a penalty shout of their own dismissed shortly after the restart. Darcheville threatened first of all at the near post and was denied by Malafeev before Ferguson claimed his rebound shot in front of goal was handled by Denisov.

Whittaker scored a superb goal against Sporting in Lisbon in the quarter-finals and he could have had the net bulging again when he met a flick from Darcheville before teeing up a well-struck shot that was deflected wide by Shirokov.

Seconds later there was more drama at the other end when Alexander raced out of his box to close down Arshavin but the Zenit man rounded the goalkeeper only to look on in disbelief as his shot was nodded off the line by Sasa Papac.

When the breakthrough came after 72 minutes Arshavin was instrumental in the opening goal, playing a one-two with Denisov who raced into the box before slotting home from eight yards, leaving Alexander with no chance.

Zyrianov almost doubled the advantage within a few minutes when his shot struck the left post, before Rangers swapped Papac for Novo in a bid to haul themselves back into the game.

Lee McCulloch, back from injury, was then thrown into the action for Hemdani with 10 minutes to go.

With time rapidly running out, Rangers' last throw of the dice came in the shape of substitute Kris Boyd but it was Darcheville and Novo who both squandered late chances to force the game into extra-time.

As they reflected on big misses, Zyrianov put the ball in the back of the net from close range to wrap up the win for Zenit.

Long-range efforts by skipper Ahmad Shahrul Azhar and Hardi Jaafar gave the Malaysian Super League outfit all three points as they avenged a 6-1 home defeat to the Singapore double winners and joined SAF on 13 points at the top of Group E.

SAF claimed first place on the basis of head-to-head results but Perak are assured of a place in the last eight as one of three best group runners-up.

Having already clinched their place in the knockout stage with a 2-0 win over Hong Kong’s Kitchee a fortnight ago, SAF fielded a largely second string squad and were put under pressure by the visitors right from the start.

Razali Umar Kandasamy sent a shot wide after finding himself in a one-on-one confrontation with goalkeeper Shahril Jantan after just two minutes and Shahrul fired just over the crossbar from 20 yards in the seventh minute as Perak mounted the early pressure.

Masahiro Fukasawa went close for the home side with a shot that came back off the crossbar in the 11th minute but it was Perak, who needed a draw to seal their progress to the last eight, who continued to show greater urgency.

And they were duly rewarded in the 21st minute when Shahrul fired a low shot from 35 yards that beat Shahril at full stretch.

Buoyed by the opener, Perak continued to press forward but left huge gaps at the back which was nearly exposed by SAF on the half-hour mark.

Ashrin Shariff was put clean through by captain Aleksandar Duric but the 25-year-old rushed his shot in a one-on-one with goalkeeper Hamsani Ahmad and shot wide from well outside the Perak box.

SAF stepped up the pressure in the second half and Khairi Zainudin was booked for a body check on Duric in the 60th minute which will see him miss the first leg of the quarter-finals through suspension.

But Perak were able to double their lead in the 69th minute.

Mario Berrios initiated the move by launching a counter-attack with a header from his own half and the ball reached Hardi Jaafar, who charged towards the SAF goal from the centre circle before blasting a long-range shot that left Shahril helpless.

SAF tried to rally for a consolation goal in the closing but lacked the cutting edge to trouble Hamsani as Perak held on for victory.