Rahul KP (76') opened the scoring for Indian Arrows, which was equalised by Achille Emana (90+1') through an injury time spot-kick. Everton Santos then took the matter into his own hands deep into the first half of extra time to score the winner for Mumbai.
Indian Arrows head coach Luis Norton de Matos made a single change to the starting XI which faced Mohun Bagan in their last I-League game as Edmund Lalrindika got the nod ahead of Rahim Ali. Prabhsukhan Gill retained his place under the sticks who was protected by a back four of Sanjeev Stalin, Jitendra Singh, Anwar Ali, and Ashish Rai. Skipper Amarjit Singh and Deepak Tangri were the two pivots in midfield. Whereas Edmund shouldered the responsibility of leading the attack.
Mumbai City FC made three alterations to their side from their last Indian Super League game against Chennaiyin FC as Mehrajuddin Wadoo and Zakeer Mundampara failed to make the cut whereas Gerson Viera had already been released by the Islanders. Amrinder Singh started in goal and was defended by a backline of Marcio Rosario, Raju Gaikwad and Lucian Goian. Everton Santos and Sanju Pradhan manned the wings whereas Balwant Singh was deployed as the solitary striker.
Mumbai started on the front-foot from the word go and it was the woodwork which denied them from taking the lead when Everton Santos' shot bounced off the far post. Minutes later, they could have finally gone 1-0 up when a flag-kick delivered by Achille Emana was headed on target by Lucian Goian. The header which looked destined to go in was cleared by Stalin from the goal line.
Arrows were banking on counter-attacks and Stalin got an opportunity to try his luck from 30-yards out after Edmund was fouled by Sahil to stop him from progressing. It was a brilliant effort from Stalin from the set-piece as the ball swerved and stooped down perfectly, forcing Amrinder to make a fingertip save.
It was even-stevens in midfield as Arrows upped their game to match their more illustrated opponents. Balwant was starved of supply and had little to work with for the bulk of the first half. As a result, the deadlock was yet to be broken when both teams headed for the tunnel at the end of first 45 minutes.
Mumbai did all they could to find inroads in a resolute Arrows defence and Sehnaj Singh almost leaked in a ball which was skied by Jitendra only to be punched half-heartedly by Gill. The clearance fell for Balwant who went for the spectacular with an overhead kick that flew into the hands of Gill.
Mumbai City were carving out opportunities but lack of creativity in the attacking third were not helping their cause. They had to utilise the flanks as anything through the middle was getting smothered by a determined Arrows defence.
Rahul stunned the men in blue by scoring a brilliant goal after showing a clean pair of heels to Goian. He latched on to a perfect through ball by Aniket Jadhav and an exquisite first touch saw Goian struggling to keep up. This time he kept his calm to roll the ball past Amrinder into the net.
Mumbai refused to give up and they were rewarded with a penalty when Rai brought down Everton inside the box after making a mess of a clearance. Emana stepped up from 12 yards and calmly converted from the spot sending Gill the wrong way.
Guimaraes' men kept piling on the pressure and Raju started to bombard the Arrows box with long throw-ins. Both Rosario and Goian got their heads to the incoming deliveries but were dealt well by the defence.
Just at the fag end of the first half of extra-time, Everton scored to put Mumbai in the lead. A long ball from Goian was brilliantly chested down by the Brazilian before releasing a bullet shot from his right foot which beat Gill even after he got his palms on the ball.
It was a professional performance from Mumbai to see out the remaining 15 minutes as they kept knocking the ball among themselves to further frustrate Indian Arrows.
With this win the Islanders progress to the Round of 16, where they will face East Bengal on April 5, at this same venue.