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The Three Lions came out on top when the sides met last summer at Euro 2020 but Germany are unbeaten since then and have made huge strides under Hansi Flick, with the hosts producing another impressive display in Munich.
An offside call denied Jonas Hofmann a goal in the first-half but he got on the scoresheet shortly after the break to put his side in front. England struggled to find a response but it came a few minutes from time as Nico Schlotterbeck brought Kane down in the box and, after a VAR review, the penalty was given.
Kane continued his incredible record from the spot to bring up a half century for England, and ensure Gareth Southgate’s side didn’t fall to back-to-back Nations League defeats. The Three Lions now have just four matches to go until the World Cup gets underway later this year.
Germany started quickly in Munich, with Kai Havertz having an effort saved after 60 seconds and Kyle Walker then producing a brilliant piece of defending to stop Thomas Muller having a tap-in minutes later.
Midway through the opening period Hofmann had the freedom of the England half and tucked the ball away past Jordan Pickford, only for the offside flag to swiftly go up.
Harry Kane had a massive chance to break the deadlock as Manuel Neuer spilled a corner to his feet, but the England captain blazed over the bar with an empty net waiting.
Bukayo Saka grew into the match in first-half stoppage-time, of which there was eight minutes, as he had a shot saved and saw another fly wide of the far post as the sides went into the break level.
Hofmann had the ball in the back of the net again shortly after the restart, and this time the officials did not come to England’s rescue. Joshua Kimmich played a lovely first-time pass into his teammate and although Hofmann fired it pretty much straight at Pickford, it hit the goalkeeper’s palm and flew into the net.
There was a brief response from England immediately after the goal, as Mason Mount had a decent strike from range saved before Raheem Sterling dragged an effort across the face of goal.
With 20 minutes to go, Pickford went some way to making up for his earlier mistake as he made a great save at his near post to keep at Muller’s well-struck volley.
Jack Grealish was introduced and had an immediate impact, playing the ball across the face of goal and Kane looked certain to score at the back post but Neuer did superbly to somehow keep it out.
The England captain would get his chance though. His penalty appeals were waved away but a VAR check eventually followed and the referee returned from the pitchside monitor to point to the spot.
Kane sent Neuer the wrong way to bring up another landmark and move to within three of Wayne Rooney’s England record of 53 international goals.