Manchester United crashed out of the Champions League following a 3-2 to RB Leipzig.

Here, the PA news agency looks back at some other European nights to forget for the Red Devils.

Basaksehir warning

United got an early glimpse of troubles ahead in their current Champions League campaign when beaten 2-1 away to Istanbul Basaksehir during November. Former Chelsea and Newcastle striker Demba Ba exploited poor United defending to score the opener for the Turkish side, with Edin Visca adding another. Although Anthony Martial pulled one back before half-time, United could not find an equaliser.

United faulty in Basel

Swiss club Basel reached the last 16 of the Champions League at the expense of an out-of-form United, who failed to make it to the knock-out stage in December 2011. Having needed only a point to progress, the Premier League champions were behind to an early goal from Marco Streller, with captain Nemanja Vidic then hobbling off injured. Alexander Frei added a second with six minutes left as Phil Jones’ late goal proved little consolation.

Jose’s touchline dash

The ‘Special One’ enjoyed a memorable night at the expense of his future employers in March 2004 as Jose Mourinho’s Porto side battled to a 1-1 draw at Old Trafford, which was enough to secure a 3-2 aggregate victory. United looked on course for the quarter-finals after Paul Scholes’ header levelled the tie and gave Sir Alex Ferguson’s side the away goal advantage overall. However, Francisco Costinha pounced on a fumble by Tim Howard to knock in a dramatic last-minute equaliser on the night – which saw Mourinho sprint from the dugout and down the touchline in wild celebration.

Welcome to Hell

During November 1993, Manchester United’s first Champions League adventure ended with a violent trip to Galatasaray. Following a feisty 3-3 draw in the first leg at Old Trafford, the United squad were given a hot reception on touchdown in Istanbul – with one of the banners proclaiming “Welcome to Hell” as Roy Keane, Bryan Robson, Paul Ince, Peter Schmeichel and Eric Cantona wandered through arrivals at Ataturk airport. The atmosphere inside the Ali Sami Yen stadium was electric, with Cantona shown a red card for arguing with the referee, and the Frenchman had to be escorted off the pitch by a police officer. A goalless draw saw United out of Europe, with players reporting scuffles with police as they went back to the changing rooms. Rocks were thrown at the United coach as it left the stadium – and Ferguson vowed ‘never to return’ to Istanbul, where more than 150 United supporters had been imprisoned and then deported following incidents around the city.

Raul on the prowl for Real

Following the triumph of their 1999 Champions League victory over Bayern Munich in Barcelona, United were knocked out of the quarter-finals by Real Madrid. An expanded tournament which included up to four of the top teams from each country saw United progress through both group stages. However, after a 0-0 draw in the first leg in Madrid, United came up short back at Old Trafford, after an early own goal from captain Roy Keane was followed by two wonderful strikes from Raul Gonzalez in as many minutes at the start of the second half. David Beckham pulled a goal back with a fine individual goal and Scholes added a late penalty – but there was no dramatic finale this time as United slumped to a first home defeat in 16 months.