A poor error by Debjit Majumder gifted the Islanders a chance to go ahead from the penalty spot in the first half. Greg Stewart obliged by dispatching the spot-kick to put his side ahead on the stroke of half-time.
The Marina Machans responded well in the second half and equalized through Petar Sliskovic, who headed home expertly from Ninthoi Meetei's cross. However, former Chennaiyin winger Lallianzuala Chhangte put Mumbai City back in front, sweeping home a loose ball in the box.
Thomas Brdaric's side still had life in them, though, and equalized right at the death through substitute Jockson Dhas' thunderous volley. However, Chennaiyin wilted in extra-time and allowed Chhangte and Stewart to score in the first 15 minutes.
Another spirited comeback followed as Rahim Ali brought the Marina Machans within a goal of Mumbai City with six minutes to play. However, Stewart completed his hat-trick on a swift counter-attack to seal a 5-3 win for his team.
Here are the player ratings from this thrilling 2022 Durand Cup clash:
Mumbai City FC
Phurba Lachenpa - 6/10
Lachenpa was reasonably solid and was thoroughly beaten for all three Chennaiyin goals.
Sanjeev Stalin - 6/10
Stalin had a busy night. He did well in defense but needed to be slightly better with his forward passes.
Mehtab Singh - 6/10
Mehtab Singh did well as Chennaiyin ramped up the pressure at the beginning of the second half. However, his positioning was poor for Sliskovic's goal.
Rostyn Griffiths - 5.5/10
Griffiths let Sliskovic escape for the equalizer and generally looked shaky until Mourtada Fall came on to relieve some of the pressure on him.
Amey Ranawade - 7/10
Ranawade made an excellent run into the box to win a first-half penalty for Mumbai City. He was also largely solid defensively but gave Meetei too much space to basically pick his man out for Chennaiyin's first equalizer.
Alberto Noguera - 7/10
Noguera was brilliant in midfield for Mumbai City, constantly switching passes to open up space for his side. He also helped out defensively when needed in the second half.
Ahmed Jahouh - 5.5/10
Jahouh delivered a good pass over the top in the play that saw Ranawade win a penalty. However, he sorely lacked creativity otherwise and his set-pieces hardly threatened Chennaiyin's defense.
Vinit Rai - 6/10
Rai added another body in attack for Mumbai City in the first half but was extremely subdued in the second period.
Bipin Singh - 6.5/10
Bipin Singh was kept quiet for much of the match, but forced the save that led to Chhangte's goal with some excellent movement and anticipation.
Greg Stewart - 9.5/10
Stewart enjoyed a fantastic night that saw him score his first hat-trick in Indian football. The Scot scored emphatically from the spot before creating the chance that ultimately led to Chhangte's first goal.
He then put his side ahead in extra-time with a beautiful finish before closing the game out with another neat goal on the counter. Stewart's passing was excellent as well and these are the kind of performances Mumbai City bought him for.
Lallianzuala Chhangte - 9.5/10
Chhangte's excellent 2022 Durand Cup campaign continued in this match. He showed excellent attacking instincts to sweep the ball into an empty net and put his side ahead in the second half.
The winger then scored with a stooping header after Chennaiyin's defense fell asleep before assisting Stewart on the counter for Mumbai City's fifth goal.
Mourtada Fall - 7/10
Fall should've gotten more on his clearance for Dhas' goal but was excellent overall after joining proceedings. He also got the assist for Chhangte's second goal.
Gurkirat Singh - 6/10
Gurkirat Singh won a couple of fouls and made some good runs but was let down by his finishing.
Vignesh Dakshinamurthy - 6/10
Dakshinamurthy did his work defensively to help Mumbai City see out Chennaiyin's threat late in the game.
Rowlin Borges - 6.5/10
Borges played some exquisite passes on his comeback from injury, one of which found Chhangte who assisted Stewart for the game-clincher.
Mandar Rao Desai - 6.5/10
Desai was sent on to add more defensive solidity and did a good job.
Gursimrat Singh Gill - 6/10
Gill made a couple of important clearances and was generally solid.
Debjit Majumder - 5.5/10
Chennaiyin deserved to go into half-time with the score at 0-0. However, Majumder's decision to tackle Ranawade, who had two defenders near him, and concede a penalty proved costly.
While he made a few good saves after that, the foul played a big part in the final result.
Aakash Sangwan - 5/10
Sangwan lacked the same potency he has showed in the 2022 Durand Cup while going forward. He was also caught out defensively for Mumbai City's opener and also made a couple of errors that went unpunished.
Narayan Das - 6/10
Das looked solid while he was at centre-back but struggled once he was sent out wide. He let Stewart onto his strong left foot far too easily for the fourth goal.
Vafa Hakhamaneshi - 6.5/10
Hakhamaneshi was Chennaiyin's best defender against the Islanders. He was aerially dominant, confident in bringing the ball out from the back and rugged in the tackle.
However, he played every Mumbai City player onside for Chhangte's goal just five minutes into extra-time and that proved to be a pivotal error.
Ajith Kumar - 5/10
Kumar's final-third delivery was poor and he was also troubled by Chhangte's quick feet. He has impressed in the 2022 Durand Cup, but this was a forgettable performance from the new arrival.
Edwin Sydney - 5/10
Sydney seemed to be given the freedom to roam around the pitch but didn't do much with the ball at his feet before being replaced at half-time.
Julius Duker - 6.5/10
Duker tried hard to keep Chennaiyin moving against Mumbai City's packed midfield and did a decent job before tiring in extra-time. He got the assist for Ali's goal with a smart pass into him in the final 10 minutes of the match.
Sajal Bag - 6/10
Bag committed a number of unnecessary fouls in dangerous areas but also did well to help Chennaiyin get on the front foot in the second half.
Anirudh Thapa - 6.5/10
Thapa played in a myriad of positions in this contest and did well at almost all of them. His corners caused chaos, with one of them leading to Ali's goal. However, his presence in the attacking third was limited for perhaps the first time in the 2022 Durand Cup.
Kwame Karikari - 5/10
Karikari had a couple of shots but ultimately departed the field with a shoulder injury after less than 20 minutes.
Petar Sliskovic - 7/10
Sliskovic didn't receive much service but did well with whatever little he got. The striker scored with a resounding header to bring Chennaiyin level in the second half and also went close a couple of times after that. His link-up play was also excellent.
Rahim Ali - 6.5/10
Ali struggled to have much of an impact in regulation-time. However, he popped up with a brilliant close-range strike to make it 4-3 before striking the crossbar after some exquisite interplay between Meetei and Sliskovic.
Ninthoi Meetei - 7.5/10
Meetei's arrival seemed to disrupt Mumbai City's defensive shape altogether. He carved them open with his darting runs and got the assist for Sliskovic's goal with a delightful cross. His cross that was half-cleared by Fall also led to Dhas' second equalizer close to the end of regulation time.
He also won fouls, corners and could've had another assist had Ali's shot in extra-time dipped by just a couple of inches.
Sajid Dhot - 5.5/10
Dhot looked solid under very little pressure in regulation. However, he wilted in extra-time when he should've taken more charge of the tired Chennaiyin defense.
Jockson Dhas - 7/10
Dhas was another fantastic impact sub for Chennaiyin. He volleyed home a brilliant equalizer with barely three minutes left before striking the crossbar with another beautifully struck shot in extra-time.
Syed Suhail Pasha - 6/10
Pasha struggled to have any real impact on the match as Mumbai City shut shop.
Senthamil S - N/A
Senthamil hardly touched the ball after coming on in the second half of extra-time.