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The game was between two sides who had a pretty easy ride in the qualifying series for the 2022 FIFA World Cup, with the Samurai Blues producing the latest shock in Qatar.
2014 World Champions Germany began their 2022 FIFA World Cup journey with defeat after an impressive Japanese side stunned the Europeans 2-1.
The Samurai Blues of Japan came from behind to register an emphatic victory after an excellent second-half performance.
Doan and Asano were the heroes for the Japanese Blues who became the latest team to produce an upset in Qatar.
A dominant first half saw four-time World Champions Germany go into the break with a deserved but narrow 1-0 lead.
Gundogan's penalty was the difference between the two teams in what was an entertaining first 45 minutes.
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Germany was the better side and created the best chances in the game but Japan also had some threatening moments of their own.
Early scare for Die Mannschaft
While Germany dominated, they survived a scare from the Samurai Blues, who were the first to put the ball in the back of the net.
As early as the ninth minute, Gundogan was dispossessed in midfield which led to a devastating break from the Japanese.
A cross from the right found Daizen Maeda, who calmly slotted home from close range. But the Germans were let off by the referee who ruled off the goal for offside.
Key moment
At the half-hour mark, having weathered the early storm and dominated after that early scare, it was the Europeans who had the chance to break the deadlock when the referee awarded them a penalty.
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Japan's goalkeeper Shuichi Gonda fouled left-back, David Raum inside the box and the referee had no other option but to point to the spot.
Gundogan stepped up to convert calmly the resultant penalty which was the difference between the two teams at the break.
Second half
The second 45 minutes started on a quiet note, with Germany still controlling proceedings at the Khalifa International Stadium.
Germany had the first real chance when Gundogan almost doubled the lead on the hour mark. But he watched as his shot came off the post.
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10 minutes later, it was Germany again who came close to adding to the scoreline but were thwarted by an excellent double save from Gonda.
Japan finally got their first chance of the half in the 73rd minute when Junayo Ito tested Manuel Neuer.
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The Bayern Munich legend was up to the task though, pulling off a one-handed save to deny the Blues.
The Equaliser
After he denied the Japanese, Neuer was powerless as Japan restored parity two minutes later.
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Neuer initially saved a shot from the left-hand side but couldn't save the rebound from Ritsu Doan, who reacted quickest to tuck home the equaliser.
Asano the hero
With seven minutes left to play, Japan took a shock lead when Takuma Asano fired in what turned out to be the winner.
Japan, playing in their seventh consecutive World Cup, takes charge of Group E with the win while Germany sits bottom of the table.
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