The Blue Tigers ' last appearance at the 2011 Asian Cup was when they had qualified through the AFC Challenge Cup route.
Goals by Rowllin Borges (28'), Sunil Chhetri (60') and Jeje Lalpekhlua (90+2') was added to by Lam Seng's bizarre own goal in the 70th minute while Nicholas Tarrao (37') was able to equalise once in the game for Macau.
India started with a 4-2-3-1 formation with Chhetri playing behind Jeje with the only surprise being Jackichand Singh starting on the right wing instead of Udanta Singh.
Needing a win to qualify by securing a top-two spot in the qualifying group for the 2019 Asian Cup to be held in UAE, the home side put Macau under some early pressure. Skipper Sunil Chhetri's first-minute cross that resulted in a corner was India's first chance. Eugeneson's ball from a short-worked corner evaded both centre-backs Anas Edathodika and Sandesh Jhingan in the Macau box.
A couple of minutes later, Chhetri's one-two with Jeje bounced back off a Macau defender and fell back into the former's path. However, before the Indian skipper could capitalise with the ball at his feet in the box, Macau goalkeeper Ho Fai smothered it.
Meanwhile, heavy rainfall began creating puddles of water on the pitch, resulting in odd bounce and thus making it difficult for the players, especially the visitors.
India kept creating chances as they searched for the opening goal. Jeje's flicked header from a long ball in the 21st minute saw Lao Kin hold back Chhetri in a bid to prevent him from receiving it in a dangerous position outside the box. The booking was followed by Chhetri's attempt that missed the top corner ever so slightly.
However, the goal eventually came for India in the 28th minute as Borges ' deflected shot off Macau skipper Chiang Ieong nestled in the back of the net after Jeje managed to spot the Goan midfielder at the top of the box. The move was initiated by Narayan Das from the left wing with a low cross that Jeje, at first, tried to backheel into the goal. Luckily enough, it came back off a defender for the Chennaiyin FC attacker to notch the assist.
But, out of the blue, India conceded the equaliser within 10 minutes. Tarrao sneaked in between Jhingan and Pritam Kotal who were caught ball-watching as Lei Hou's cross from the right wing was headed in by the Macau number 10 in the 37th minute.
The second half resumed with Constantine throwing in Balwant Singh in place of Jackichand Singh as India switched to a 4-4-2 with the new man partnering Jeje up front. Narzary moved on to the right wing and Chhetri was deployed on the left wing.
Balwant clearly had an impact on the game as his clever running of the channels had the Macanese defenders scampering all over and India started to find a lot of space.
The Blue Tigers almost regained their lead in the 59th minute, but Jhingan's header off Lyngdoh's outswinging corner was tipped for a corner by a diving Ho Fai.
Come the hour mark and India were back in front when a Macanese defender chested down a long ball aimed at initiating an Indian counter but failed to control the ball. Jeje took it in near the halfway line and sent Balwant clear. The substitute raced forward before squaring the ball into the box for Chhetri to knock it in.
It almost immediately became 3-1 as another mixup between the Macanese defenders saw them allow a long ball to bounce and Balwant pounced on it. But Ho Fai was quick to reduce the angle on the eventual shot that went wide.
Soon enough, however, Macau made it easier for India by gifting a goal in the 70th minute. Narzary's rather poor cross from the right was made a hash of by Lam Seng. His attempted clearance ended in a disaster for his side as the ball looped over the goalkeeper off his knee and landed in the back of the net.
That was not to be the last goal of the match as Jeje , who had an attempt blocked in the 78th minute and missed another in the 87th minute, made amends by converting a pass from Chhetri during an injury time corner to lend an emphatic touch to the scoreline.