Glasgow City win 1-0 in Moscow but Hibs slump to 4-1 loss to Slavia Prague
Hibernian and Glasgow City had mixed fortunes in the first legs of the Women's Champions League last 32.
Hayley Lauder's 11th-minute goal was enough for City to take a 1-0 lead back to Scotland against Chertanovo Moscow.
But, despite taking an early lead through Siobhan Hunter, Hibs suffered a 4-1 defeat by Slavia Prague.
A hat-trick from Czech Republic striker Tereza Kozarova and a fine drive from Andrea Jarchovska put the visitors in an almost unassailable position.
It is only the second time in history that two Scottish sides have reached the knockout stages of the competition and never before have two teams made it to the last 16.
Hibs always had the tougher task against a side that have graced the quarter-finals three times in the past four years.
But, in front of a crowd of 1287 in Leith, Hibs initially threatened a major shock when Hunter thumped them ahead inside two minutes.
Slavia responded to the defender's sixth goal in three games and, in a nightmare seven minutes, Hibs conceded three times.
Tereza Kozarova twice found a gap in Hibs' defence to score before even goalkeeper Jenna Fife at full stretch could not get near Jarchovska's long-range strike.
Shannon McGregor shot wide and had a header saved, while Amy Gallagher's fierce shot was well tipped over by goalkeeper Olivie Lukasova.
Fife's brilliant block to deny Katerina Svitkova only delayed the fourth goal and, on 75 minutes, Kozarova completed her hat-trick.
Hibs have it all to do in the second leg on 25 September, while City host Chertanovo at Petershill Park the following evening.
'Score unfair on Hibs'; City's Booth unhappy - reaction
Hibernian head coach Grant Scott: "It is one of these situations where it feels like the score flatters them, but ultimately they've had the chances and they've taken them really clinically.
"Each and every one of them we could have done better on. I felt we contained and minimised the opportunities that they had, so it is a wee bit difficult to swallow that one.
"We need to stop them scoring early over there and give ourselves a chance. They are a quality side and at the moment we are out of the tie, but an early goal for us might give them some doubts."
Glasgow City head coach Scott Booth: "It's great to be able to get a win, but I don't think we played well enough and Chertanovo showed they can be dangerous on the break.
"It's going to be a very difficult game at home. It is a slightly difficult position given the opposition worked really hard, they stay narrow and they make it difficult to find space and play through them.
"It was just one of those nights where the standards weren't there and the quality of our passing was definitely not there and there were too many loose passes."