James Holland was unable to guide LASK Linz to a UEFA Champions League play-off upset against Club Brugge on Wednesday (AEST), while Ajax held on for a goalless draw at APOEL.
The fringe Socceroos midfielder played the full 90 minutes against the Belgian giants and will ultimately rue his side's profligacy in front of Simon Mignolet's goal.
LASK, who qualified as a result of their second-placed finish in the Austrian Bundesliga, tallied 15 attempts for the match, but it was Brugge defender Simon Deli who ironically went closest to scoring, nearly turning the ball beyond the former Liverpool shot-stopper.
In the end, an early penalty from Hans Vanaken was enough to hand the visitors a slender first-leg advantage ahead of next Thursday's return leg at Jan Breydel Stadium.
Ajax meanwhile named a strong starting XI that included several stars from their eye-catching 2018-19 campaign, but they produced a lacklustre and ill-disciplined performance, earning seven yellow cards and one red for Noussair Mazraoui.
Last season's Champions League semi-finalists looked the better of the two teams in the first half, but their display was lacking the decisive touch in front of goal.
After the break, APOEL began to offer more of a threat themselves and went agonisingly close in the 58th minute, when Giorgos Merkis' header hit the crossbar.
Andre Onana was then forced to make a stunning save 11 minutes later, getting down to palm away a Lucas Souza effort that was destined for the bottom-right corner.
Things got even more testing for Ajax towards the end when Mazraoui was shown a second yellow card for a needlessly clumsy tackle from behind, but they held on nonetheless.
Ajax will host the Cypriot club in Amsterdam for the second leg next Thursday.
In the day's other play-off clash, Slavia Prague claimed a 1-0 away victory over Cluj.