India were down 0-1 in the seventh minute with Emmanuel Sanchez scoring off a spot-kick award, but the hosts went on to dominate the visitors, ranked 38 places above them, with some slick passing and quick attacking moves.
India, who led 3-1 at the half-way stage, scored their goals through Narayan Das (18th minute), Chhetri (26th), Jeje Lalpekhlua (34th) and Jackichand Singh (58th).
Chhetri, who had given away his captain's armband to Norway-based towering custodian Gurpreet Singh Sandhu for this game, paved the way for two goals and also struck once to emerge as the star player for the home country.
India have not beaten higher-ranked teams often in the past and had even lost 1-2 to Afghanistan in the SAFF Cup in Kochi in January.
This victory, albeit against a none-too-strong-looking Puerto Rico side, which had arrived here only last evening and clearly looked tired after their long journey, thus must have pleased national coach Stephen Constantine who included several youngsters to prop up the team.
The spot-kick was put in by the tall medio Sanchez who beat Indian custodian and match skipper Gurpreet to bulge the bottom right corner of the goal.
This early reversal galvanized the hosts, ranked 152 as compared to their rivals' 114, into an attacking mode and they started attacking with gusto with the midfield prompting the two front-liners with down-the-middle passes.
(REOPENS DEL 65)
A free-kick was awarded just outside the penalty area following the hacking down of medio Bikash Jairu by a rival defender.
Chhetri curled the free kick around the "wall" only to hit the left post, but defender Narayan Das, lurking nearby, pounced on the rebound and struck home, finding the right corner of the goal.
Six minutes later another free-kick award was given to the home team when Chhetri was brought down by Emmanuel D'Andrea.
But on this occasion the ball struck the inside of the woodwork and then went in much to the delight of the crowd of around 7,000 fans rooting for the Indian team vociferously as suddenly India were 2-1 up.
It could have been 3-1 for India in the 32nd minute had Jeje not ballooned his shot from inside the area over the post after being fed superbly by Jackichand Singh.
However, luck and some poor defending by Puerto Rico smiled on the Indians as a high cross from Pritam Kotal was headed towards Jeje by Chhetri and the 25-year-old from Mizoram made no mistake with a simple header from an unmarked position very close to the rival goal.
Changing ends, India widened the lead after surviving a close shave when Puerto Rican midfielder Micheal Ramos struck the post with a powerful shot on the run.
The 4-1 cushion was provided by the diminutive livewire Jackichand who blasted into the underneath of the cross-piece before his shot went in. He got hold of a misdirected header from Lyngdoh before connecting the volley home.
Both teams had their chances to score in the remaining time, but neither could score any more goals and the home crowd trooped off happy after witnessing the first big game at this new venue in the western suburbs.
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