Former European champions Celtic and AC Milan were left with work to do to reach the Champions League group stage after their play-off first leg games on Tuesday.
While AC Milan will approach next week's second leg at home to PSV Eindhoven having secured a 1-1 draw and more importantly an away goal Celtic slumped to an embarrassing 2-0 defeat away at unheralded Kazakh outfit Shakhter Karagandy.
Two other sides in action fared far better on their travels, Spanish outfit Real Sociedad winning 2-0 at Lyon while a hat-trick by Roman Shirokov eased Zenit St. Petersburg to a 4-1 win in Portugal over Champions League debutants Pacos de Ferreira.
PSV exposed Milan's rustiness - they have not yet started their league season - several times in the early stages but still went behind to a Stephan El Shaarawy header on the quarter-hour mark.
The Dutch side more than held their own despite their youth - the back four's average age was 19 1/2 - and deservedly got an equaliser on the hour as Tim Matavz pounced on an error by Milan goalkeeper Christian Abbiati.
Milan coach Massimiliano Allegri was relieved to have got a draw, but added that Milan's problems were far from over.
"It is a good result but given the problems we had in the first-half and the rhythm of the match which PSV imposed on us we must be very wary with regard to what lies in store in the second leg," he said.
"It will take a good team to beat this PSV side, who are a young and very promising side."
His PSV counterpart Phillip Cocu said that their fluent, attacking football strategy would not change for the second leg, given the problems it had caused their opponents.
"Prior to their goal we were head and shoulders above them," said the former Dutch international.
"Having equalised we are still in with a chance. We had six players who are less than 21 years of age in the team this evening and they showed great maturity.
"We were fluent in our passing and movement and a vivacity and liveliness that put our opponents off their game."
Celtic manager Neil Lennon still held out hope that his Scottish champions could recover from one of their more embarrassing defeats of recent times and reach the group stage.
The hosts - whose traditional sacrificing of a sheep on the eve of the match brought its' reward - scored through captain Andrei Fionchenko and Sergei Khizhnichenko to take a healthy-looking advantage to Scotland for the second leg.
"I don't know how many chances we had tonight - clear cut ones as well - and if you don't take your chances then you make life difficult for yourself," said Lennon, who guided the side to the last 16 last season.
"However, it's not over yet. We have to go back to Celtic Park and we're not down and out just yet."