He had also been a member of the Kansas City Chiefs of the National Football League (NFL) and the Winnipeg Blue Bombers (CFL).

At Bismarck he was a three time all-state and all-conference selection and in 2003 was named North Dakota Gatorade High School Player of the Year.

[1] As a senior, he caught 75 passes for 1,274 receiving yards while being named to the North Central Conference's all-star team for the fourth season in a row.

Because of his value as a receiver, the Roughrider coaching staff pulled him from the kick return game and only used him in critical situations on special teams.

Ken Miller, the Saskatchewan head coach, and Paul LaPolice, the offensive coordinator, used many different formations in order to get Dressler the ball, from the slot back position, to wideout, to handoffs.

[17] On August 27, after clearing NFL waivers,[18] Dressler was offered contracts from the Saskatchewan Roughriders, Calgary Stampeders[19] and Ottawa Redblacks.

[23] However, on August 28 Dressler instead agreed to a contract with the Roughriders[24] that is reputedly worth a pro-rated $200,000 CAD for one year, sizeably less than the Redblacks offer.

[25] In his return to Saskatchewan on August 31, 2014, Dressler had three receptions for 28 yards in a 35-30 win over the Winnipeg Blue Bombers in the Labour Day Classic.

On September 21, 2014, Dressler recorded 125 receiving yards in a win over the Ottawa Redblacks, a game where he returned another punt for a touchdown.

Dressler tied the all-time number one record (CFL and NFL) for the most two point conversions caught in a single game by one player at two in a 31-24 loss to the Calgary Stampeders on October 3, 2014.