Arsenal reached the Champions League quarter-finals for the first time since 2010 following a tense penalty shootout victory over Porto in the round-of-16 second leg.
The Gunners had early opportunities to take the lead but Porto stood firm to keep the score at 0-0. However, it was Leandro Trossard who opened the scoring for Arsenal on 41 minutes to level the tie with a fine finish.
Mikel Arteta's side looked to double their advantage in the second half as substitute Gabriel Jesus saw his effort kept out by Diogo Costa with what was his first touch. However, extra-time was needed to settle the tie.
Neither side could find a goal needed to win the tie as it headed the distance to penalties. Gunners shot stopper David Raya proved to be the man of the moment, denying Wenderson Galeno from 12 yards to win the penalty shootout for the North Londoners.
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Story of the match
Following Arsenal's 2-1 victory over Brentford at the weekend, Arteta made just one change which saw Raya, who was ineligible against his parent club, return in-between the sticks.
As for Porto, an unchanged starting eleven was named by manager Sergio Conceicao from their 3-0 win away at Portimonense. It was also the same side that defeated the Gunners in Portugal three weeks ago.
With a one-goal deficit needing to be overturned, Arsenal dominated the opening exchanges and had an early chance on three minutes when Trossard's cross was headed over by Ben White.
However, surprisingly, it was Porto that had more possession and were looking to keep the Arsenal attack quiet.
Despite that, Bukayo Saka found space inside the penalty area but saw his shot parried by goalkeeper Costa.
The home side started to gain some momentum as a first-time drive from captain Martin Odegaard hit the side netting.
Meanwhile, Porto had a rare opportunity when Evanilson capitalised on a William Saliba mistake but the forward could only strike wide.
Evanilson continued to threaten for Porto as he tested Raya in the Arsenal goal, who was on hand to deny the Brazilian.
Despite the early chances, Arteta's side were struggling to break Porto down, who were doing their best to make things difficult for the Gunners.
With 41 minutes on the clock, the away side's resistance was finally broken when Arsenal made the all-important breakthrough. A delightful pass from Odegaard set away Trossard, who took a touch before slotting home in style to level the tie on aggregate.
Following a cagey start to the second half, the home side had their tails up and were determined to double their advantage. A Declan Rice strike blocked by the Porto defence was the Gunners best chance in the opening 15 minutes.
Arsenal had the ball in the back of the net in the 67th minute when Odegaard capitalised on a loose ball to dink the ball in the back of the net. However, the goal was ruled out for a foul on Porto defender Pepe by Kai Havertz in the build-up.
Meanwhile, up the other end, Porto broke away on the counterattack as a strike from Francisco Conceicao stung the hands of Raya.
Another chance soon went begging for the Gunners when Saliba headed over the bar.
As the match approached the closing stages, Jorginho made way for Gabriel Jesus, who almost made an instant impact by scoring with his first touch, but the forward was denied by the goalkeeper.
Arsenal were looking more likely to score a second but Saka's curling effort was saved before the rebound from Odegaard went wide of the target. Despite a dramatic second half, neither side could find a winning goal as an extra 30 minutes beckoned at the Emirates.
The tie very much hung in the balance in extra-time with Arsenal looking to finally get a much needed second whilst Porto were more than capable of hitting the Gunners on the counterattack.
On 101 minutes the first real chance of extra-time came to Porto substitute Mehdi Taremi who saw his effort go wide. Porto continued to frustrate Arsenal whilst the Gunners struggled to threaten in front of goal as the tie needed to be settled by penalty shootout.
It would be the first time since the 2016 final that a Champions League knockout stage game went to penalties.
Odegaard stepped up first for the home side and sent the goalkeeper the wrong way before winger Pepe scored for Porto to make it 1-1.
The next player to take for Arsenal was Havertz, who calmly slotted home. However, Wendell was unable to score as Raya guessed the right way with Saka successful with his penalty to make it three out of three from the spot for the home side. Marko Grujic converted from 12 yards to keep it alive for Porto.
However, for Arsenal, a powerful spot kick from Rice put the Gunners on the brink of the quarter-finals. Wenderson Galeno was next up for the visitors but Raya proved to be the hero as the Spaniard guessed the right way to secure Arsenal's spot in the quarter-finals.
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Player of the match - David Raya
Of course there only had to be one man worthy of player of the match which is goalkeeper David Raya.
The Arsenal goalkeeper will no doubt have gained popularity amongst the fans after his display against Porto.
During the 120 minutes of action Raya made some key saves to keep Mikel Arteta's side in the tie and ensure the Gunners had every opportunity to win the match.
However, the Spaniard took matters into his own hands by saving two penalties to send the Emirates into raptures. A night to remember for Raya.