Not since 2005 have Manchester United entered the playoffs of the Champions League. On that occasion, the likes of Wayne Rooney, Cristiano Ronaldo and Ruud van Nistelrooy were all on the scoresheet in a 6-0 aggregate victory over Hungarian side Debrecen.
Ten years on and the Red Devils find themselves in a similar scenario, with Belgian outfit Club Brugge their opponents this time around.
The first leg will be played at Old Trafford tomorrow evening, with the return clash at the Jan Breydel Stadium penned in for eight days later.
Ahead of those two encounters, Sports Mole has taken a closer look at what Louis van Gaal's United will be up against when they take on Blauw-Zwart.
How they reached this stage
It seemed that Brugge were destined to exit the Champions League at the third qualifying round stage when Panathinaikos won the first leg at the Apostolos Nikolaidis Stadium 2-1. But, armed with Boli Bolingoli-Mbombo's away goal when they returned to home soil for the second clash, Brugge produced a memorable performance.
It took until the second half, but from the moment that Dion Cools put Brugge 1-0 up in the 53rd minute, there was only ever going to be one winner. Further goals from Victor Vazquez and Obbi Oulare added gloss to the scoreline.
Although 2014-15 ended with a first trophy in 10 years, there was still a sense of disappointment. It seemed for a long while that Brugge were going to be crowned champions, particularly after they sat top of the pile with 30 games of the regular season played. But, in the Championship Playoffs they lost four of their 10 encounters, surrendering the title to Gent in the process.
Nevertheless, there was success in the Belgian Cup, where Anderlecht were defeated 2-1 in a dramatic final. New Newcastle United striker Aleksandar Mitrovic drew Anderlecht level in the 89th minute, but deep into stoppage time Israeli playmaker Lior Refaelov secured a 2-1 victory for Brugge.
Overall, Brugge played a record 63 matches last term, owed largely to their form in the Europa League. They went on a run of 15 matches without defeat in that competition before losing to eventual runners-up Dnipro Dnipropetrovsk at the quarter-final stage.
There is a belief among the Belgian media that the exertions of last season have taken their toll on the Brugge squad this time around. After all, they had just a month off before they returned to pre-season training in June.
The victory over Panathinaikos was the undoubted success so far, but aside from that, there has not been too much to get excited by. The Super Cup was lost to Gent, while newly-promoted Sint-Truiden ran out 2-1 winners on the opening weekend.
Seven points from a possible 12 is viewed as an adequate return, but they can at least take confidence from the fact that they overcame Kortrijk last time out thanks to Tuur Dierckx's stoppage-time winner.
While Brugge have never won a major European trophy, that does not mean that they haven't made an impact.
They remain the only Belgian club to have reached the final of the European Cup back in 1978, when they lost out at Wembley to Liverpool and Kenny Dalglish.
Two years earlier they also faced the same opposition in the final of the UEFA Cup, but once again it was Brugge that lost - this time 4-3 on aggregate after an entertaining two-legged contest.
Since then there has been semi-final appearances in both the UEFA Cup and Cup Winners' Cup, while last year's run to the last eight of the Europa League was both unexpected and impressive in equal measure.
As a player, there was once a stage when Michel Preud'homme was regarded to be one of the best goalkeepers in world football. Indeed, at the 1994 World Cup in the USA, he was named the winner of the Yashin Award as recognition for his performances between the posts at the tournament.
He also had success in European competition when he kept goal for Mechelen during their shock 1-0 win over Ajax in the final of the 1988 Cup Winners' Cup.
Since hanging up his gloves and moving into management, the 56-year-old has won trophies in the Netherlands, Saudi Arabia and his native Belgium. Preud'homme's exploits with Brugge last year earned him the Belgian Professional Manager of the Year accolade.
Three key players
Tom de Sutter
The 30-year-old recently agreed a move to Bursaspor, but he has delayed the switch to Turkey to help Brugge overcome United. Having arrived from Anderlecht in 2013, De Sutter found the net 12 times during his first season and then followed that up with another 13 goals last term.
Having advanced through the famous La Masia academy alongside the likes of Lionel Messi, Cesc Fabregas and Gerard Pique, it's still regarded somewhat of a surprise that Vazquez opted to ply his trade in Belgium. A creative midfielder with a keen eye for goal, the 28-year-old found the net 11 times in all competitions last term on his way to being named the Belgian Footballer of the Year.
At the age of 38, a footballer could be forgiven for taking things a little easier. But, with captain Simons, that isn't the case. Preud'homme once told the club's official website that whenever the holding midfielder eats a big meal at a restaurant, he runs the last few miles home while his wife drives. Such dedication to fitness meant that he missed just one match last term.
The city-owned Jan Breydel Stadium, which was opened in 1975, has a capacity of 29,042. Originally known as the Olympiastadion, it was renamed in the late 1990s after Jan Breydel, who is a folk hero from 14th century Brugge.
Located in a residential area a couple of miles outside of the city centre, the ground hosted three Euro 2000 group matches and then the quarter-final tie between Spain and France - a game that the latter won courtesy of goals from Zinedine Zidane and Youri Djorkaeff.
As well as Club Brugge, the stadium is also the home of city rivals of Cercle Brugge, who were relegated from the top division in 2014-15.
Read Sports Mole's preview of the first leg at Old Trafford here.