Chances came few and far between from both sides inside the first half at the Levi’s Stadium, with opportunities from Jesse Lingard and Gareth Bale but didn’t look to be a breakthrough until a late strike from Lingard gave United a narrow lead.
The beginning of the second period was just as lacking in opportunities, but a penalty from Casemiro in the 68th minute brought scores level. Marouane Fellaini had an excellent opportunity towards the normal time, but his skyward effort meant that the clash would go to penalties.
What arrived was one of the worst shootouts in recent memories as; Anthony Martial, Mateo Kovačić, Scott McTominay and Óscar Rodríguez missed the opening four penalties before Henrikh Mkhitaryan broke the deadlock, Luismi Quezada brought things level but further misses from Victor Lindelöf and Theo Hernández meant Daley Blind's effort gave United the edge and the decisive miss from Casemiro gave them another victory.
Starting off slow
On paper there looked to be a classic on the cards in San Francisco as the two European champions came head-to-head, but in reality it did have the makings of a pre-season friendlies as neither side were going full throttle and that showed in the lack of chances.
The first look at goal came from The Red Devils who looked to continue their unbeaten during their time across the Atlantic, Martial did well to cut it across to Lingard who let rip from outside the box and Keylor Navas did well to push it away from his goal.
Real Madrid never produced a chance of real recognition but began to prove dangerous as the first-half went on, Bale though he looked offside as he received the long ball on the right he looked to cause concern with his cross looking for Karim Benzema but Phil Jones was there to clear.
Lingard tested the waters once again with four minutes to play, Marcus Rashford did well to open the space for Lingard to rip once again from outside the area but it goes just wide of Navas’ left-hand post.
Drawing first blood in quite some style
It looked like that both sides would go into the break all square despite the quality picking up towards the break, but José Mourinho’s men managed to take the lead right at the death and in some style.
It had been good tour thus far for Martial but he managed to up a gear in the 46th minute as he cut in from the left, the young Frenchman took four Madrid players out of the game with his silky footwork and it was simple enough to square it across to Lingard who tapped it into an empty net.
Handed an avenue back into the game
Like the first period it took a while for the second-half to get off the ground, but Zinedine Zidane’s men were handed a golden opportunity to get back into the game after Lindelöf’s recklessness.
Hernández burst down the left as he made strides into the area and the Swedish defender timed his tackle horrendously as he sent Hernández flying and the referee had no option but to point to the spot. It was Casemiro who stepped up for the set piece, and Brazilian made no mistake as he coolly slotted past David De Gea
As the clock began to tick down both sides look for the winning goal that if anything would end the contest quickly and remove themselves from the punishing Californian heat, and with six minutes to play United should of found themselves ahead.
It was excellent play from Scott McTominay as he whipped a great cross into the area which was straight into the feet of Fellaini, the Belgian was left completely unmarked in the centre of the area but he somehow sent his miscued volley well over the crossbar.
Not one for the history books
Though the fixture lacked the competitiveness of that of a European final, the pressure of a penalty shootout was still in the air and it was clear that it got to some of the players as the first four penalties were far from the target.
Martial was the first to step up and after his excellence in the first period many would have backed him to open the scoring, but it was sent straight over the crossbar. Kovačić was the first up for Madrid and De Gea showed his long suitors what they were missing as he did well to beat away the Croatian’s effort.
McTominay looked to break the duct and it looked good as he picked out the bottom corner but Kiko Casilla did well to keep it out. Anything that Casilla could do De Gea could do better, it was Rodríguez who stepped up but the keeper did well to guess right and send it high and wide of danger.
Mkhitaryan was having a great tour thus far and it was the Armenian who drew first blood as he coolly sent Casilla the wrong way, the lead didn't last long however as though De Gea guessed right with Quezada's effort even getting a hand to it there was too much power behind it to keep it out.
Lindelöf looked to redeem himself for his earlier mistake by giving The Red Devils the advantage, but his effort rounded off a terrible afternoon for the 23-year-old as he hit straight down the middle which Casilla cleared with ease. Lindelöf's victim for the penalty Hernández was up next, he managed to fool De Gea as he looked for the Spaniard's opposite corner but fooled himself as it went well wide of the post.
It was Blind who stepped up next and he gave Mourinho's side the edge as he followed a similar route down the middle to Lindelöf’ but fooled Casilla leaving Casemiro with it all to do. The Brazilian had scored from the spot in normal time, but he couldn't replicate that with the pressure on as he sent it well over the crossbar.