Chennaiyin FC defeated Mumbai City 2-0 in the Hero Super Cup Round of 16 clash, knocking the Islanders out of the tournament. Though we had a good run against Chennaiyin FC in the the two league matches, the Islanders couldn’t repeat the feat for a third time. Goals from CK Vineeth and Jeje Lalpekhlua sealed a quarter-final spot for Chennaiyin FC.

The Islanders started off strong with attacking intent. A cross from Sanju Pradhan got us in Chennaiyin FC’s box very early in the game but it was out of Alen’s reach. Chennaiyin FC’s strong attack was suppressed by the boys but they conceded a corner which was easily cleared.

As the match progressed, the Islanders continued with their attack with long passes and crosses but failed to make the most out of it. Raynier Fernandes tried to gain possession from Christopher Herd but ended up getting a yellow card for an aggressive tackle.

The Marina Machans had a chance to score with a free-kick from Isaac but it was stopped by a brilliant save from Ravi Kumar. At the hour mark, Chennaiyin FC managed to put the ball in the back of the net but the linesman raised his flag and ruled it out for offside.

John Gregory made an early change by replacing Isaac with Thoi Singh. The Islanders were looking to dominate in midfield with Rafique leading the charge but he too went into the book for a bad challenge on Jeje.

The first half which looked like ending at 0-0 suddenly turned on its head with 2 goals in 2 minutes from CK Vineeth and Jeje Lalpekhlua doing the damage. CK Vineeth scored with a curling effort and Jeje finished off with a first time finish. All the good work from the Islanders went for a toss in a couple of minutes.

The Islanders began the second half with a two-goal deficit as the Boss made a double change with Joyner Lourenco and Pranjal Bhumij replacing Vignesh Dakshinamurthy and Milan Singh.

Experienced centre-back, Lucian Goian nearly pulled one back for the Islanders in the 48th minute as he smoothly controlled the ball on the edge of the box before going for seeing his shot go wide of the goal. At the other end, Ravi Kumar was forced into a save from CK Vineeth's long range effort.

Despite having majority of the ball possession, the Islanders were lacking the finishing touch to get back into the game. The boys were giving their all and to put Chennaiyin FC on the backfoot. In the 63th minute, Souvik Chakrabarti was booked for a mistimed tackle and the frustration was being shown on the field.

A few minutes later, Bipin showed good skills to beat his marker and send a cross towards the six-yard box. The ball bounced awkwardly ahead of Pranjal and he was unable to keep his header on target. Just a minute later, Pranjal was shown a yellow card for a bad foul on substitute Dhanpal Ganesh.

While the Islanders pushed ahead in numbers, once again it was Lucian Goian who came closest to a goal. He made an attacking run and mnearly found the far post but his effort was inches away. In the final change, Sanjay Balmuchu came on the impressive Raynier Fernandes who ran the show in midfield.

Despite putting their everything, the Islanders failed to find the back of the net and were left disappointed after a spirited performance at the Kalinga stadium. A mixed season comes to an end with a semi-final finish in Hero ISL 2018-19 and an early exit in the Round of 16 of the Hero Super Cup.