It was not the best start for Canada in the power play, but they soon found their rhythm when Barbados-born Nicholas Kirton and Shreyas Movva came into the fold, scoring 49 and 37 respectively, before Barry McCarthy got them both out in his 2-24.
They fizzled out shortly after, finishing with 137-7, though it soon became clear an upset was on the cards as Ireland stumbled to 59-6 in the 13th over, thanks to Canada's impressive bowling.
A strong display from George Dockrell (30 not out) and Mark Adair (34), paired with fielding mistakes, set up a nervy finish. However, Adair was then taken by Jeremy Gordon (2-16) in the final over to ensure Ireland would finish short of their target with 125-7.
Ireland stay bottom of Group A with no points, while Canada are right in the mix, level on two with Pakistan.
Meanwhile, Scotland continued their strong start to the World Cup with their first win of the tournament, a five-wicket victory over Namibia on Thursday to move them top of Group B.
Data Debrief: History made for Canada
Before this game, Canada had lost each of their last five men's T20Is; they had lost only four of their 23 games prior to this run in the format (W18 T1). However, that run has now ended in perfect fashion.
For just the second time, Ireland have lost their opening two games in the ICC Men's T20 World Cup; only in 2016 did they do the same in a single edition of the tournament.
An enticing meeting on Wednesday in New York awaits as India, one-time winners of this tournament in 2007, aim to start with victory.
There will be further inspiration for Rohit Sharma's white-ball team, who will part ways with the experienced Dravid after the conclusion of the World Cup.
"It is going to be the last one that I am in charge of," Dravid said at his pre-match press conference, confirming his intention to leave.
"Unfortunately, the kind of schedules and where I find myself at this stage in my life, I don't think I'll be able to re-apply.
"This will be my last one. But having said that, [the significance of the tournament is] no different for me.
"I love doing the job. I've really enjoyed coaching India and I think it's a truly special job to do, and I enjoyed working with this team and it's a great bunch of boys to work with."
India were somewhat overpowered by big-hitting T20I stars as they exited in 2016 and six years later.
Yet the early results in this tournament suggest placid conditions will bring bowlers back into the contest, and Dravid hopes his side can take advantage.
"We can't say that we've not played good cricket in these tournaments," he added. "Yes, we probably haven't been able to get across the line in that one knockout game.
"Hopefully we play good cricket to get ourselves into those positions again. Then maybe play good cricket on the day to get across the line.
"But the important thing when you start these tournaments is not to think about that. It is to actually think about getting into those positions again.
"I think that's as hard as actually winning those games at times. You have to find yourselves in those positions where you are pushing for glory, and that's all you can do as a group and as a team.
"Our whole goal will be to try and get ourselves once again into a position where we give ourselves a chance to be able to win a tournament."
India have triumphed in all seven completed T20Is between these two teams, yet Ireland captain George Dockrell hopes to utilise the home contingent in the United States.
He said: "There's such great Irish roots in America, definitely in New York, so it would be nice to get a good turnout from the locals – a bit of green in the crowd to back us would be welcome."
