Dundee United suffered the joint-heaviest European defeat in Scottish football history when they went down to a 7-0 thrashing by AZ Alkmaar.

United are the second Scottish side to fall at their first hurdle in the Europa Conference League qualifiers following Motherwell’s 3-0 aggregate defeat by Sligo Rovers.

Here, the PA news agency looks at five of the previous worst nights for Scottish clubs in Europe.

Artmedia Bratislava 5 Celtic 0

Gordon Strachan’s Parkhead reign could not have got off to a worse start in 2005 as the Hoops were thumped in a Champions League qualifier in Slovakia. They trailed 1-0 at the break, but the roof caved in during the second half as Juraj Halenar’s hat-trick sealed the club’s worst result since a six-goal drubbing by Kilmarnock in 1963. Strachan’s men threw everything at Artmedia back in Glasgow but crashed out 5-4 on aggregate.

Aberdeen 1 Sigma Olomouc 5

As a member of the Gothenburg Greats, Mark McGhee played a part in the Dons’ greatest ever triumph with their 1983 Cup Winners’ Cup final success against Real Madrid. But his first match as Aberdeen boss in 2009 ended in humiliation as their Czech visitors ran riot at Pittodrie in the Europa League qualifiers. Aberdeen slumped again 3-0 in the return leg  as they surpassed their previous worst European aggregate defeat – 5-0 against eventual European champions Liverpool in 1981.

Hibernian 0 Malmo 7

Hibernian were the first ever British club to play in European competition when they marched all the way to the semi-finals of the inaugural European Cup in 1955, but the club’s proud history suffered a dent 58 years later when they were humiliated 9-0 on aggregate by the Swedes. A campaign that would eventually end in relegation started just as painfully as Pat Fenlon’s side were crushed in front of a shell-shocked 16,000-strong Easter Road crowd.

Progres Niederkorn 2 Rangers 0

Pedro Caixinha splashed out £8.5million in 2017 as Gers fans got set for their first European adventure in six years, but it was not enough to guarantee safe passage beyond Luxembourg’s part-timers. Kenny Miller gave the Light Blues a narrow first-leg lead after a nervy Ibrox clash, but disaster struck inthe grand duchy. Needless to say, Caixinha did not last much longer.

Kilmarnock 0 Connah’s Quay Nomads 2

New Rugby Park manager Angelo Alessio endured a nightmare home debut in 2019 as the Welsh underdogs overturned a 2-1 first-leg deficit. Rugby Park was hosting its first European tie in 18 years and  two second-half goals, coupled with a red card for Stuart Findlay, saw Killie fans come crashing back to earth following the highs of the Steve Clarke era.