Reigning FA Cup champions Manchester United booked their place in the fourth round by beating Arsenal on penalties.
The first half on Sunday was marred by a lack of quality from both teams, and Gabriel Martinelli came close before his shot was disallowed for offside.
The match came to life after the break with United as Bruno Fernandes put the visitors ahead before United's momentum was halted when Diogo Dalot was sent off for a second booking. Arsenal then quickly found the equalizer through a deflected Gabriel volley.
The Gunners then had a golden chance to take the lead after being awarded a penalty, but Altay Bayindir made a good save to deny Martin Odegaard from 12 yards.
After a tense additional 30 minutes, the match was decided by penalty kicks, with a miss by Kai Havertz giving Ruben Amorim's team the pass.
Mail Sport's ISAAN KHAN was in the Emirates to provide his expert analysis on both teams.
Man United secured their place in the FA Cup fourth round by defeating Arsenal on penalties
Altay Bayindir rejected Kai Havertz's penalty and gave his team the victory in the shootout
ARSENAL (4-3-3):
David Raya (6)
They had a comfortable first half but could do nothing to prevent Bruno Fernandes' goal at the beginning of the second half. Crucial save when he ducked to deny Joshua Zirkzee a goal later on. He went in the wrong direction for all five penalties.
Jurrien Wood (7)
One of the few bright sparks for Arsenal. He tried to make things happen and was impressive on the right wing. Replaced in the 100th minute by Thomas Partey.
Guillermo Saliba (7)
Defensively solid and reliable as always, but he will be punished for the way his team allowed United to hit them on the counter-attack.
Gabriel Magalhães (6.5)
A rare mistake by the Brazilian that led to United's goal, but he made up for it with a solid shot for Arsenal's equalizer. The most relieved man underground.
Gabriel Magalhaes equalized Arsenal again, but should have done better with United's first goal
Academy product Myles Lewis-Skelly continues to impress at left back in the absence of Riccardo Calafiori
Myles Lewis-Skelly (6.5)
The 18-year-old kept Oleksandr Zinchenko and Kieran Tierney out of the team and impressed again until he was replaced by Leandro Trossard at the start of extra time.
Martin Odegaard (6)
More touches than anyone else in the game, but he missed the crucial penalty that would have given Arsenal the tie in normal time. He converted his penalty in the shootout.
Jorginho (6)
One of only three Arsenal changes that Mikel Arteta made and he did what was expected of him, controlling the pace of the game, without doing anything special.
Mikel Merino (5)
He was largely absent in a first half in which he completed just seven of Arsenal's 204 passes. It has to show more. Taken off by Declan Rice in the 73rd minute.
Gabriel Jesus (5.5)
He came on for Leandro Trossard and offered a threat until he was stretchered off in the 40th minute due to a serious injury. He joins Bukayo Saka and Ethan Nwaneri on the sidelines.
Kai Havertz (4)
Only he knows how he failed two assistants with the game 1-1 when it was more difficult to fail than to score. You could say he also dived to win the penalty. And he missed his penalty in the shootout.
Gabriel Martinelli (6)
Good finish in the first half, but it was miles offside. Didn't cause enough problems in the final third as Arsenal failed to exploit their man advantage.
Martin Odegaard was constantly involved but missed from 12 yards to put Arsenal in front.
Gabriel Martinelli was quiet in the closing stages as Arsenal failed to capitalize on their numerical advantage.
Kai Havertz endured a dismal night, missing a sitter before seeing his penalty saved in the shootout.
Substitutions
Raheem Sterling (7)
He replaced Jesus in the 40th minute and looked orderly when he came on, regularly offering threats.
Declan Rice (7)
He came on for Merino and made the difference, forcing two brilliant saves. Maximum penalty.
Leandro Trossard (6)
He replaced Lewis-Skelly at the end of normal time and came within inches of scoring the winner.
Thomas Partey (6)
Go ahead for Timber in extra time. Good penalty.
Kieran Tierney (6)
Jorginho came on in the 113th minute.
UNUSED: Neto, Kiwior, Zinchenko, Butler-Oyedeji
Manager: Mikel Arteta (6)
Will will wonder how his team didn't win this in regulation time. His changes made the difference, but Arsenal was wasteful and this was further proof that they need a quality striker.
MAN UNITED (3-4-2-1):
Altay Bayindir (9)
He could have done better in the build-up to Arsenal's equalizer but he made an impressive save from Martin Odegaard's penalty and a few more afterwards. United's hero in the penalty shootout.
Matthijs De Ligt (7)
Part of a United back three that was largely solid. Unfortunately, Gabriel's goal took a wicked deflection, but he made an incredible clearance to deny Trossard extra time.
Harry Maguire (7)
He seemed comfortable and the penalty against him was tough. Other than that, he did nothing wrong and can be proud of a brilliant performance. Blooming under Amorim.
Altay Bayindir produced his best performance in a United shirt to keep the visitors in the game.
The influence of Ruben Amorim has benefited Harry Maguire, who was very solid in defense.
Lisandro Martínez (6.5)
Like De Ligt and Maguire, he defended well. He was booked in the 29th minute for a foul on Jesús and had to be very careful after that.
Noussair Mazraoui (7)
Exceptional and clearly one of the strongest players under Amorim. Relentless throughout the match and showed his versatility, switching sides with Diogo Dalot at half-time.
Manuel Ugarte (6)
He fought very well throughout the game despite Arsenal dominating possession. Thrown out by Tyrell Malacia at the start of extra time.
Kobbie Mainoo (6)
Together with Ugarte, he had a good turn. Another United player who was booked in the second half by Andy Madley and replaced by Toby Collyer in the 80th minute.
Diogo Dalot (4)
Amorim switched him and Mazraoui at half-time and it was costly. Within 15 minutes, Dalot received two silly cards and was sent off. Arsenal equalized immediately afterwards.
Alejandro Garnacho (7)
Given the nod from Amorim, Amad Diallo was not completely fit and was excellent. He chose Bruno Fernandes in goal for United and showed his defensive attributes with Dalot out.
Bruno Fernandez (7.5)
Booked for sarcastically removing his boot in the first half after not being awarded a foul, but his finish for United's goal was of the highest class. In his day, a special footballer.
A tireless display from Bruno Fernandes helped United reach the penalty shoot-out despite being under attack.
Alejandro Garnacho was given a rare start under Amorim and was instrumental in United's equaliser.
Rasmus Hojlund failed to make an impact on the game before being replaced by Joshua Zirkzee.
Rasmus Hojlund (5)
He couldn't sniff out his battle with Arsenal's centre-backs. Just the 16 touches before Joshua Zirkzee connected at the end of regulation.
Substitutions
Amad Diallo (7)
Garnacho came on in the 80th minute and it was all action as always. He scored in the penalty shootout.
Joshua Zirkzee (6.5)
He replaced Hojlund in the 80th minute and nearly scored the winning goal in extra time. He converted the winning penalty in style.
Toby Collier (6.5)
Curiously, he preferred Casemiro, when he replaced Mainoo. It was impressive.
Tyrell Malacia (6)
He replaced Ugarte in extra time and made a change at left back.
Leny Yoro (6.5)
He came on for Maguire in the 104th minute. He scored in the penalty shootout.
UNUSED: Onana, Eriksen, Casemiro, Antony
Manager: Ruben Amorim (7)
Another weekend where you can be proud of your team's performance. He made some key changes after Dalot's red card as his team fought until the end. Another big step in the right direction.
REFEREE
Andy Madley (3)
The perfect advertisement for the VAR since it made several mistakes. He lost control of the game in the second half and should not have given Arsenal a penalty.