Rangers have it all to do in the second leg of their UEFA Cup first round tie if they are to progress in the competition, following a 1-0 defeat against Portuguese side Maritimo.
Under-pressure manager Alex McLeish watched his side slump to their eighth successive European tie without a win, despite creating numerous scoring chances, particularly in the first half.
But an end-to-end first half finished with Maritimo going into the break with a 1-0 lead thanks to a goal from Gustavo Manduca, leaving Rangers to lament a handful of missed opportunities.
On 27 minutes Leo Lima, who had been a constant danger to the Rangers defence throughout the first half, fired straight at the Rangers goal. Stefan Klos parried the shot, but Manduca latched on to the loose ball and slammed in from close range.
The visitors had survived several early scares as Jean Alain Boumsong scrambled a clearance from a Mitchell Van der Gaag header and a Lima free-kick skimmed past the upright after seeming to take a deflection.
After ten minutes Novo went down in the area but the referee denied Rangers' penalty claims. Two minutes later Novo picked up a cross from Fernando Ricksen but sent his attempt wide.
Midway through the half Dado Prso used his height advantage and skimmed the left post with a header following a Chris Burke free-kick.
But at the other end Lima beat Dragan Mladenovic to the ball and set up the opening goal.
Maritimo were the stronger side in the second half and Rangers keeper Klos was under heavy pressure for much of the period.
Early in the half defender Tonel miss-hit his strike from close range and much to Rangers' relief that ball went high over the bar.
Lima and Manduca continued to terrorise the Rangers defence. On 60 minutes Lima shot narrowly over the bar and seconds later Klos was at full stretch to tip behind a Manduca shot from 20 yards.
Substitute Paolo Vanoli tried an opportunist strike from long range five minutes from time as Rangers pressed for an equaliser, but his shot went over the crossbar.