Aberdeen suffered Europa League heartache as they narrowly lost 1-0 away to Portuguese giants Sporting Lisbon.
The Dons held their own for long spells, but lack of cutting edge and composure in the final third saw them unable to secure a breakthrough after falling behind to a goal from Tiago Tomas after just eight minutes.
It is the sixth time in the last seven seasons under boss Derek McInnes that Aberdeen have crashed out of the Europa League at the third qualifying round stage.
Aberdeen have previously exited at that stage to Real Sociedad (2014), Kairat Almaty (2015), NK Maribor (2016), Apollon Limassol (2017) and HNK Rijeka (2019).
In narrowly losing in Lisbon, the Dons missed out on a clash against LASK of Austria in the play-offs at Pittodrie next Thursday.
LASK defeated DAC 1904 Dunajska Streda of Slovakia 7-0 in their tie.
Sporting’s build up to the match was hampered by a Covid-19 outbreak at the club.
Nine players and manger Ruben Amorim were ruled out of the third qualifying round tie as they were self-isolating having tested positive.
Such was the extent of the outbreak, Sporting relocated to a training camp in the Algarve in a bid to keep the transmission under control.
Sporting’s league opener against Gil Vicente at the weekend was postponed due to the outbreak.
Aberdeen had to sweat until the day of kick-off to discover for definite if the tie would go ahead.
Dons boss Derek McInnes made three changes to the side that crashed 3-0 to Motherwell 3-0 on Sunday.
Coming in were Shay Logan, Tommie Hoban and Dylan McGeouch, with Funso Ojo, Niall McGinn and Dylan McGeouch all dropping out.
There was also no Scott McKenna, who was also absent from the loss to Motherwell.
Scotland international McKenna completed a transfer to Championship side Nottingham Forest on the eve of the Euro tie in a £3 million deal that could rise to £5m with achievable add-ons.
Disaster struck in the eighth minute when Sporting went ahead as Luciano Vietto disguised a pass towards TOMAS, who broke into the box.
The 18-year-old burst past Andy Considine before unleashing a superb 12 yard drive beyond keeper Lewis.
It was a hammer blow for the Dons to concede so early.
In the 13th minute, a cross from the right from McGeouch curled awkwardly and Sporting keeper Adan pushed over.
Defender Ash Taylor rose to meet the resultant header, but his effort was straight at the keeper.
In the 35th minute Marley Watkins delivered a dangerous ball behind the defence from the right, but the on-running Ryan Hedges was agonisingly short of connecting 15 yards out.
Keeper Joe Lewis came to the rescue in the 39th minute with a superb, and brave, diving save at the feet of Jovane Cabral to block his close range shot.
Aberdeen were fortunate not to be two behind in the 56th minute when Tomas was found completely unmarked 12 yards out.
Tomas was allowed plenty of time, but his header went wide.
It was a let off for the Dons.
Just after the hour mark, Hayes burst down the left flank, but rushed his shot which blasted wide and high of Lisbon’s goal.
In the 77th minute, Lewis raced off his line to save from Cabral.
Aberdeen pushed on and Hedges’ low drive from the edge of the penalty box was deflected of Coates and flashed inches in front of Watkins with the goal beckoning.
The Dons had a clear chance to level in the 86th minute when substitute Scott Wright found Hedges with a perfectly weighted through ball.
However, Hedges sliced his left-footed drive wide from 15 yards. It was Aberdeen’s best opportunity of the game and he had to at least get it on target to test the keeper.
ABERDEEN: Joe Lewis, Tommie Hoban, Ash Taylor, Andy Considine, Shay Logan, Jonny Hayes, Dylan McGeouch, Ross McCrorie, Lewis Ferguson, Ryan Hedges, Marley Watkins.
Subs: Scott Wright (for McGeouch 69), Ryan Edmondson (for Watkins 81), Connor McLennan (for Logan 83),
Subs not used: Tomas Cerny, Ronald Hernandez, Funso Ojo, Niall McGinn.
Sporting Lisbon: Adan, Coates, Neto, Feddal, Porro, Luiz, Wendel, Mendes, Tomas, Vietto, Cabral.
Subs: Sporar (for Tomas 77), Branganca (for Wendel 86),
Subs not used: Paulo, Plata, Joao Silva, Antunes