Rangers' undefeated run in Europe this season came to an end when they suffered a 2-1 loss to Hapoel Tel Aviv in the first leg of their round of 32 match in the UEFA Cup in Israel.
The home side took the lead through an impressive free-kick by Salim Toama just before the break before Nacho Novo hauled Rangers back into the game, adding to the goals he had already scored in the tournament against Livorno, Auxerre and Maccabi Haifa.
But Baruch Degu ensured the win for the Israelis when he grabbed the winner with 15 minutes to go - just when it looked as though Rangers would hold on for a crucial draw.
Tonight's reverse also means the current crop of players have failed to better the club record of 12 European games without defeat, which was set by Walter Smith's side during his first spell as manager in the 1990s.
Smith made three changes from the side who defeated Kilmarnock in the Bank of Scotland Premier League at the weekend.
Kevin Thomson and Ugo Ehiogu were ruled out after both picked up hamstring injuries at Rugby Park, while Charlie Adam was dropped to the bench.
In came Gavin Rae, Karl Svensson and Novo.
Hapoel were fortunate not to fall behind early in the game when a poor pass back from Walid Badir put goalkeeper Shavit Elimelech under pressure and his attempted clearance cannoned off the body of Novo.
Unfortunately for Rangers, the striker could not take advantage of the error and the opportunity was lost.
Rangers then found themselves under pressure when Hapoel were handed a free-kick just outside the box but Yossi Abuksis' effort was cleared by the Gers defence.
Izbita Ogbona then saw his effort flash wide, before Rangers goalkeeper Allan McGregor was called into action to block a 25-yard shot from Katzor Wellington.
At the other end, Novo was not too far away when he met a Chris Burke cross only to send his header across the face of goal and wide.
Rangers were threatening again when a Burke corner was met by David Weir on the six-yard line but the defender nodded just over the crossbar.
Burke then picked up the first booking of the game for a challenge on Dani Bondar with half an hour gone.
Rangers had another chance to snatch the lead before the break when Burke released Kris Boyd into the box but his effort was blocked by Ram Doani.
Instead, it was Hapoel who opened the scoring after 42 minutes when Weir fouled Ogbona just outside the box.
And McGregor had no chance when Toama sent a stunning free-kick curling into the back of the net.
Hapoel tried to double their advantage within a few minutes of the restart but Ogbona's effort was weak and easily smothered by McGregor.
Rangers then claimed a Weir header was handled in the box by Ram but the penalty pleas were ignored by referee Pedro Garcia.
The Ibrox side were back on level terms anyway with 53 minutes gone.
A Barry Ferguson free-kick on the edge of the box took a slight deflection and rebounded off the post but Novo put the ball in with his knee.
There were a tense few moments for Hapoel when goalscorer Toama was carried off on a stretcher following a challenge from Svensson but he was quickly back involved in the action again.
Hapoel should have reclaimed their lead soon after when Elyaniv Barda met Toama's corner and blasted over from close range.
Burke went to ground in the box with 20 minutes to go but the claim for a penalty was a weak one and the referee signalled for play to continue.
The Ibrox side then suffered a blow when Hapoel reclaimed their lead with 15 minutes to go.
Barda's effort looked to be heading wide of target but Degu burst into the box and slid home from seven yards, leaving Rangers facing a far more difficult task in the second leg in Glasgow next week.
