That's when the veteran slotback makes his first-ever appearance at Mosaic Stadium as an opponent when Winnipeg visits the Saskatchewan Roughriders. The five-foot-seven, 187-pound Dressler spent his first eight seasons with the Riders before being released this off-season and joining the rival Blue Bombers.
"It will be different from any other game, I've accepted that,'' Dressler said last week while in Toronto doing promotional shoots for the upcoming CFL season. "For me, it's going to be controlling those emotions and keeping everything in check so I'm performing to the best of my abilities throughout that game.''
In January, new Saskatchewan coach/GM Chris Jones released Dressler and defensive lineman John Chick in a salary-cap move as the two were scheduled to make $500,000 combined in 2016. But the move hit a nerve with Riders supporters as both were fan favourites and instrumental in the franchise's 2013 Grey Cup win on home soil.
Dressler came to Saskatchewan in 2008 and was the CFL's top rookie that year. Over eight seasons, the 30-year-old native of Bismarck, N.D., recorded 539 catches for 7,792 yards and 50 TDs.
The two-time CFL all-star recorded five 1,000-yard receiving seasons. He's third in all-time receiving yards and fifth overall in receiving touchdowns.
Chick and Dressler weren't unemployed long. Dressler signed a two-year deal reportedly worth $350,000 with Winnipeg while Chick joined the Hamilton Tiger-Cats.
Dressler's desire was always to finish his CFL career in Saskatchewan - his fiancee is from Regina. But the CFL salary cap and free agency were always constant reminders of just how difficult that would be to accomplish.
"Being in this league for eight years you see it every year, you know how it works,'' Dressler said. "I've seen guys who're more than capable of playing being released or traded.
"As a player you're always aware of what can happen and ready for what may happen.''
Especially after a club revamps its front office and coaching staff following a 3-15 campaign just two years after a championship.
"When you bring in an entire new staff almost from the top down you always know something different will be going on so you kind of prepare for it,'' Dressler said. "Maybe (I wasn't) fully prepared until it happened but I understood at all times what the possibilities might've been.''
And that included maybe one day donning rival Winnipeg's colours.
"That's so small in the scheme of things compared to not playing,'' Dressler said. "As a player in that situation I just wanted to play football.''
But for the first time since '09, Dressler will go to training camp without Saskatchewan's Darian Durant at quarterback. However, Bombers' starter Drew Willy was Durant's backup (2012-13) and offensive co-ordinator Paul LaPolice served as the Riders' receivers coach and offensive co-ordinator (2007-09).
"We definitely built that QB-receiver chemistry and got to the point where we pretty much always knew we were seeing the same things,'' Dressler said of Durant. "To be able to use that on the field can help create an advantage and it will be hard to leave that behind.''
Durant, coming off season-ending elbow and Achilles injuries the last two years, admits life without Dressler will be tough.
"This is a guy I started with, our careers started together,'' Durant said. "Throughout the years we always talked that once we reached a certain age then one of us was going to have to go sooner or later.
"I'm just glad he's found another home. He's in a familiar situation with coach LaPo and he's with a familiar quarterback with Drew Willy. I still think (Dressler) has a lot left in the tank, he can continue to produce.''
Dressler is looking forward to a fresh start in Winnipeg, which has missed the CFL playoffs the last four years and hasn't won the Grey Cup since 1990.
"As a player, first and foremost, you want to play for and be part of a team that wants you there and wants you to be a part of what they're doing,'' he said. "Obviously with an entire new staff being brought into Saskatchewan, they have their vision of what they want to do and the types of players they want.
"I'm happy to be in Winnipeg and have the experiences I've had with coach LaPolice. I haven't played with (Willy) for a couple of years and obviously we don't have a ton of in-game experience together but I look forward to working with him and building that.''