The 34-year-old Toronto native is keen not to let another opportunity slip away, and two days before Canada opens its next phase of World Cup qualifying at Cuba, De Rosario was quick to point out he and his teammates can't take a single moment for granted.
"The older guys, the more experienced guys on the team, we definitely share that with them, that you never know when it will be your last chance," De Rosario said after practice at BMO Field.
"You see how unfortunate it was for Josh Simpson to take a knock before this. Stuff like that, you never know when your chance is in front of you. So we always tell these guys, 'Make the best of it, you're representing your country and your community.'"
Simpson is out indefinitely after breaking his leg less than two weeks ago during a game in Switzerland.
The 77th-ranked Canadians play No. 145 Cuba at Havana on Friday to kick off a qualifying round that has traditionally given them trouble.
Canada failed to survive this stage for the 2010 World Cup after picking up just two of nine possible points at home and losing all three games on the road.
De Rosario, who is tied with Dale Mitchell in all-time scoring for Canada with 19 goals, said despite the pressure of qualifying, he's still managing to have fun.
"You have to enjoy it, that's where the best of you comes out is when you're enjoying the game," he said.
"Obviously in the back of your mind you know that there is a demand and a sort of expectation that we're expected to do very well. But you have to enjoy what you're doing, you have to play with that enjoyment on the field, and I think when we do play like that, we're at our best."
Canada faces a few unique challenges against Cuba. Coach Stephen Hart said he has little scouting intel on a team that trotted out its under-23 side for two friendlies against Jamaica that Hart had travelled to to watch.
There's also concerns about the pitch and the weather, which could be scorching with a 2 p.m. scheduled kickoff.
"The pitch we're not sure about, we got pictures of it and it looked OK, but until you step on it, looks can be deceiving," Hart said, hours before the team boarded its flight to Havana.
The Canadians could get a break in the weather. The forecast is calling for rain Thursday, and clouds and a high of 30 C on Friday.
Hart said it's key that Canada maintains its organization and discipline to deal with anything the conditions throw at them.
"We need to be measured and calculated because it's going to be extremely hot — sunny and hot or wet and hot," Hart said. "We have to take care of the things we do well and cut down on potential errors, and just try to be as efficient as possible."
Hart and his players were buoyed by their recent friendly against the United States — a 0-0 draw Sunday at BMO Field in Canada's only game with its full side this year.
"You look at the U.S., they've had seven or eight games together as a team, so for our first game, and a real test, we did an exceptional job," De Rosario said. "We held off a very potent U.S. attack, you could see the way they play, they have a good understanding of each other. . .
"I think we did a good job of sticking to our gameplan and also creating some goalscoring chances as well."
Atiba Hutchinson practised Wednesday after sitting out Friday's game with a knee injury. Hutchinson travelled to Cuba but Hart said the midfielder for Dutch team PSV Eindhoven would likely need a couple more days of practice before he could play.
Hutchinson said it's crucial Canada kick off this next phase with a victory against Cuba, and the key will be for the Canadians not to stray from their more organized style of game.
"All the games in this group stage will be tough away from home especially, we don't know what to expect from Cuba really, we expect they'll be athletic, physical, maybe not so well-organized," Hutchinson said.
"We're going to have to make sure we keep our shape, good on the ball, creative, create some attacking chances in the final third and hopefully get some goals and three points."
The Canadians host Honduras on Tuesday at BMO Field. The top two teams in the group will advance to the final round of qualifying in the CONCACAF region, which covers North and Central America and the Caribbean.