But mostly Younger's post-season experience versus Montreal has been bitter disappointment, a trend the veteran safety hopes to change Sunday when the Toronto Argonauts face the Alouettes in the East Division final.
"I've been in the league nine years and was fortunate enough to win a Grey Cup my first year but spoiled in the sense I thought that was just going to be how it was," Younger said following Tuesday's practice at Rogers Centre. "It's been eight years since I've been back and that's a long time.
"When you think about everything I've been through leading up to this moment, I'm just first thankful to have it again and don't want to waste it."
As a rookie, Younger helped Toronto earn a 26-18 road win over Montreal in the East final before downing B.C. 27-19 in the Grey Cup game in Ottawa.
But since then, the Alouettes have sent Younger packing in the playoffs — 2005, '06, and 2010 with Toronto and '08 with the Edmonton Eskimos.
"You respect the fact they've earned the right to compete against you, the ultimate opponent in that sense as far as my career is defined," Younger said. "I know they'll be ready to play.
"When they get that bye week, their preparation is always top notch and at a high level so it's exciting because you know you're opponent is worthy. They're the man and if you want to be the man you've got to beat the man. It won't come easily but you don't want it to."
Montreal (11-7) finished atop the East Division and is hosting the conference final for the fourth time in five years and ninth time since 2000. The Alouettes are looking to make their ninth Grey Cup appearance in 13 seasons.
But a Toronto win would give the Argos definite home-field advantage for the 100th Grey Cup on Nov. 25 at Rogers Centre.
Toronto (9-9) finished second in the East and advanced to the division final with a 42-26 home win over Edmonton last Sunday. The Argos lost the season series to Montreal 2-1, their lone victory being a 23-20 decision at Molson Stadium on July 27.
Montreal and Toronto meet at Olympic Stadium on Sunday, with more than 42,000 tickets already been sold. The 2004 East final there attracted more than 51,000 spectators and Younger can't wait to return to that hostile environment.
"I want the crowd in it, that's what makes it special and memorable," he said. "I remember in '04 it was like leaving a nightclub because my ears were ringing two hours after the game.
"That's something I look forward to, being the enemy in another team's home arena.''
Toronto's defence was solid against Edmonton, registering a fumble recovery and an interception to set up two touchdowns in the Argos' record 31-point outburst in the second quarter. The Eskimos scored 16 points in the fourth after the outcome was decided.
Montreal's offence presents a much more formidable challenge.
Als quarterback Anthony Calvillo, the CFL's second-leading passer this season, anchors a unit that was second overall in passing while finishing tied with B.C. for fewest sacks allowed (30). The Argos will have to disguise their coverages if they hope to confuse Calvillo, a 19-year veteran who has pretty much seen it all over his illustrious career.
"With Anthony you've got to give him a lot of different looks, you've got to find a way to put some pressure on him and you can't let him get comfortable," said Argos head coach Scott Milanovich, who was an assistant in Montreal and coached Calvillo for five seasons before coming to Toronto. "If he knows what coverage you're in you're going to be in trouble and he'll get you.
"We'll have a lot in, the guys are used to it now because they've played against him three times but(Argos defensive co-ordinator Chris Jones) will have to do a great job of continuing to change his looks while still putting pressure on Anthony."
Montreal running back Brandon Whitaker, the CFL's rushing leader last year, is out with a season-ending knee injury. Predictably, the Alouettes ground attack — ranked second-last — has struggled without Whitaker, but Milanovich isn't overlooking that.
"To me, it's always stop the run first," he said. "If you can get them in a situation where they have to throw it every down and they can't rely on that then it becomes a little bit easier to call defences.
"We need to stop the run first but obviously we've got to be aware of Anthony."
Younger said the Argos will present many different looks to Calvillo, hoping their pass rush can get to him before he gets set or at least force him to take more time to decipher the defence and thus create a coverage sack or pressure.
"They'll see some of the same stuff, they'll see a bunch of different stuff," Younger said. "Most importantly, you've got to try and keep Calvillo on his toes, disguise everything and hold the disguises because you know where his football IQ is at. A huge challenge.
"They run a top-notch program so everybody they have out on the field is a capable football player, they don't have any slouches. But I don't think we do either."
The 34-year-old Younger is the elder statesman of Toronto's secondary, its most experienced CFL veteran and lone player over the age of 30. All of which makes Younger better appreciate the opportunity the Argos currently face.
"I understand what type of opportunity we have ... the awareness of knowing the moment is everything you want as an athlete," he said. "It's going to be two good teams and we're going to have to raise our level because of the success they've had and how long they've played together.
"If it's Xs and Os it's their coaching staff versus our coaching staff, if it's their receivers versus our DBs, their front seven versus our front seven, whatever it is, we've got to find a way to match what they're doing."