Rangers were made to pay for poor defending as they surrendered an early lead and went down 2-1 to Jagiellonia Bialystok in Poland in the Europa League.
Derek McInnes’ first European tie as Rangers manager began in ideal fashion in the first leg of the third qualifying round when home defender Guilherme Montoia diverted a Tuur Rommens cross into his own net after only four minutes.
But Kajetan Szmyt equalised in the 13th minute with a goal that could have been avoided, unsettling the Light Blues, and he struck again eight minutes later after another lapse at the back from the visitors.
McInnes introduced Cammy Devlin, Nico Raskin and Findlay Curtis at the start of the second half, and although Rangers controlled possession after the interval, they could not find an equaliser. Curtis hit the post in added time, and the Scottish side must now overturn the deficit at Ibrox next week.
Daisuke Yokota, the winger signed from Hannover, made his debut and had only a few touches before Rangers took an early lead.
Left-back Rommens linked up with midfielder Mohamed Diomande down the left, and his ball across the area was missed by striker Youssef Chermiti. However, the unfortunate Guilherme Montoia could not move his feet in time, and the ball bounced off him from six yards before rolling over the line.
In the 10th minute, Chermiti tested Jagiellonia goalkeeper Slawomir Abramowicz with a long-range effort, and at that stage things looked encouraging for the Govan side.
However, Rangers’ lead was wiped out when Szmyt, with no immediate threat apparent, curled an effort towards goal from the edge of the box and it travelled all the way through before going in at the far post.
Rangers’ problems deepened when midfielder Thelo Aasgaard’s flick on the edge of the home side’s penalty area was intercepted, setting Jagiellonia away on a rapid counter-attack.
When Nik Prelec sent a cross into the box, Rangers defender Emmanuel Fernandez slipped in front of goal, allowing Jesus Imaz an attempt which goalkeeper Ivor Pandur pushed away, but Szmyt reacted quickest to score his second.
Kajetan Szmyt’s double condemned Rangers to defeat.
In the 37th minute, more shaky defending — this time from Dujon Sterling, who gave the ball away — allowed Rodrigo Conceicao to break clear, but he drove his shot into the side-netting despite having options in the middle. Prelec then saw an effort parried clear by Pandur, who also denied Norbert Wojtuszek just before half-time.
McInnes made three substitutions at the interval, sending on Devlin, Raskin and Curtis in place of Dan Neil, Tochi Chukwuani and Yokota, and the momentum shifted.
Diomande set up Devlin in the 59th minute, but he was crowded out before Curtis guided a Raskin delivery inches wide.
Soon afterwards, with Rangers maintaining the pressure, Devlin’s 20-yard shot was tipped over by Abramowicz, though the resulting corner came to nothing. Then, in the 68th minute, Imaz failed to hit the target from 12 yards at the other end.
Abramowicz also saved from Curtis, and the Rangers substitute later volleyed against the post as the visitors created several more openings in a strong finish, but the tie will now have to be decided next week in Govan.