Real Madrid have left a trail of destruction on their march to European glory down the decades, but there is a large tract of land that remains mostly unconquered: Germany.

In their first 25 UEFA club competition trips to Germany between 1966 and 2014, they lost 18 times and won just once – against Bayer Leverkusen in 2000. In 2013/14, a 6-1 last-16 victory at Schalke and 4-0 semi-final success away to Bayern München sandwiched a 2-0 reverse at Borussia Dortmund that still took eventual champions Madrid into the semis. However, Wednesday's 2-0 upset at Wolfsburg revived unhappy memories.

Hamburg 5-1 Real Madrid

1979/80 European Cup semi-final second leg

Madrid had one foot in the final, to be played at the Santiago Bernabéu, after beating Hamburg 2-0 in the opening instalment of this last-four tie. Yet, in what is considered HSV's finest hour (and a half), those dreams were shattered. The first-leg advantage was erased inside 16 minutes by a Manfred Kaltz penalty and trademark Horst Hrubesch header.

And though Laurie Cunningham replied, come half-time Hamburg were in the box seat after further efforts from Kaltz and Hrubesch. Caspar Memering's last-minute strike merely sealed Madrid's fate. "The fans didn't want to go home, staying in the stadium for around an hour," recalled defender Ditmar Jakobs. "It was the best HSV match of all time."

Hamburg went on to lose to Forest in the 1980 final ©Getty Images

Kaiserslautern 5-0 Real Madrid

1981/82 UEFA Cup quarter-final second leg

In a quarter-final with distinct echoes of that Hamburg match, Madrid arrived in Germany with a two-goal first-leg cushion – 3-1 on this occasion – yet were back to square one in no time. Friedhelm Funkel's early brace gave Kaiserslautern an away-goals advantage and Madrid, the wounds of two years earlier reopened, simply imploded.

Isidoro San José and Cunningham were sent off before the interval, and after Ronnie Hellström saved Rafael García Cortés's penalty, Francisco Pineda followed them down the tunnel midway through the second period. All the while the Red Devils kept picking off visitors captained by Vicente del Bosque, with Hannes Bongartz, Norbert Eilenfeldt and Reiner Geye all scoring.

Borussia Mönchengladbach 5-1 Real Madrid

1985/86 UEFA Cup third round first leg

Mönchengladbach's Bökelbergstadion was too small to accommodate the hordes wanting a glimpse of Madrid so this last-16 tie was switched to Dusseldorf, where the 65,000 crowd were not disappointed. Amid driving rain, Jupp Heynckes's side did not so much make themselves at home as raid the fridge, light a fire and fall asleep in front of the TV.

Frank Mill's strike and José Antonio Salguero's own goal put Mönchengladbach 2-0 up at the break, and better was to follow. "In the second half we completely outclassed them," said Uwe Rahn, who notched twice before Ewald Lienen added another. A consolation from Rafael Gordillo, later red-carded, would somehow prove decisive though, as Madrid subsequently won 4-0 at home to prevail on away goals.

©Getty Images

Bayern München 4-1 Real Madrid

1999/2000 UEFA Champions League second group stage

On paper, the Merengues were favourites, yet twice in nine days in February/March 2000 Bayern tore up the script. They triumphed 4-2 at the Santiago Bernabéu before bettering that result a week later, displaying the ruthless streak that would serve them so well en route to 2001 European glory.

Madrid went two down inside the first half-hour in Bavaria after goals from Mehmet Scholl and Giovane Elber. Iván Helguera raised hopes of a comeback, only for substitute Alexander Zickler to sink them with a double in what was Lothar Matthäus's farewell outing for Bayern. Still, both teams would qualify from the section, with Madrid destined to knock out Bayern in the semi-finals (even if they lost 2-1 in Munich).

Bayern München 2-1 Real Madrid

2000/01 UEFA Champions League semi-final second leg

It was a closer affair 12 months later. Elber had already secured a 1-0 victory at the Bernabéu when his header eight minutes into the return left Bayern firmly in the driving seat. And if Luís Figo's swift response kept Madrid in contention, home coach Ottmar Hitzfeld's tactic of soaking up pressure and hitting the visitors in transition worked perfectly nonetheless.

Jens Jeremies earned the hosts breathing space before half-time, rifling in following Scholl's tapped free-kick, and Madrid were out. "The team performed fantastically. To beat Real twice is sensational. We have completed a small miracle," said Hitzfeld, whose side overcame Valencia in the final.

Borussia Dortmund 4-1 Real Madrid

2012/13 UEFA Champions League semi-final first leg

This was Madrid's sixth straight defeat on German soil and certainly one of the most comprehensive as Robert Lewandowski crushed José Mourinho's men, the Pole becoming the first player to notch four goals in a UEFA Champions League semi-final. The only surprise amid the post-match inquests was how Madrid, through Cristiano Ronaldo, had briefly restored parity either side of half-time.

"Something clicked in the second half," said BVB coach Jürgen Klopp. "I've never seen such a great goal as Lewy's third – absolutely amazing. It was a great experience that will live in the memory for everyone involved, no matter what happens in the return leg." His charges conceded twice late on in a 2-0 second-leg loss in Madrid yet there was no undoing this performance.

Log in for free to watch the highlights Watch highlights of Wolfsburg's win

Wolfsburg 2-0 Real Madrid

2015/16 UEFA Champions League quarter-final first leg

Madrid may have been seeking progress from the quarter-finals for the 27th time in 33 attempts but they came unstuck against opponents at this stage for the first time. "After Madrid's early goal was ruled out, I initially thought: 'Oh God, what's going to happen here tonight?'" Maximilian Arnold said of Cristiano Ronaldo's offside strike, yet by the 25-minute mark it was the 21-year-old midfielder firing Wolfsburg 2-0 in front.

Seven minutes earlier Ricardo Rodriguez had converted a penalty after André Schürrle was felled by Casemiro, Madrid custodian Keylor Navas's record of never shipping a UEFA Champions League goal not surviving his first trip to Germany. Instead it was Wolfsburg's Swiss keeper Diego Benaglio starring with a fine string of saves.

It has not been all doom and gloom for Madrid in Germany, however ...

Bayer Leverkusen 2-3 Real Madrid

2000/01 UEFA Champions League group stage

Madrid's lone success from their first 25 visits to Germany came in 2000, when they did it the hard way. Twice Vicente del Bosque's team fell behind in this matchday two fixture, with Bernd Schneider and Michael Ballack scoring, only for Roberto Carlos and Guti to equalise.

Roberto Carlos then hit the winner 15 minutes from time, capitalising on Jens Nowotny's error and powering in. It was the only time in 144 appearances in UEFA competition that the Brazilian left-back registered twice in a game.

Bayern München 0-4 Real Madrid

2013/14 UEFA Champions League semi-final second leg

Madrid put their German woes behind them, at least for a while, 12 months after their exit to Dortmund. In the round of 16 they hammered Schalke 6-1 in Gelsenkirchen to herald a 9-2 aggregate success, and although they succumbed 2-0 at Dortmund in the quarters, they had won 3-0 at home. They then travelled to Munich with a slender 1-0 semi-final lead, and within 20 minutes Sergio Ramos had struck twice, with Ronaldo netting a third.

That was Ronaldo's competition-record-breaking 15th of the campaign and he added another at the death to inflict Bayern's record home European defeat, saying: "I think a lot of people thought we were going to come here and not be able to score." Last term Madrid then made it three victories in four away matches in Germany with a 2-0 last-16 triumph at Schalke – however, Wolfsburg have now made it 20 losses for the ten-time champions in 30 trips.