Scheifele grew up playing minor hockey in his hometown of Kitchener, Ontario, playing for the Kitchener Jr. Rangers rep program in the Alliance Pavilion League. After his minor midget season in 2008–09, Scheifele was drafted by the Ontario Hockey League 's Saginaw Spirit in the seventh round, 134th overall, of the 2009 OHL Priority Selection. The following season, Scheifele was assigned to his hometown Kitchener Dutchmen Jr.B. club for a year of seasoning in the Greater Ontario Junior Hockey League. After the 2009–10 season, on August 16, 2010, Scheifele's playing rights were traded by the Spirit to the Barrie Colts in exchange for goalie Mavric Parks. Two weeks later, Scheifele signed with the Colts for the 2010–11 season. In TSN mid-season prospects' ranking ahead of the 2011 NHL Entry Draft published in January 2011, Scheifele was projected to be drafted 21st overall. Ultimately, he was selected seventh overall by the Winnipeg Jets, the organization's first draft pick since relocating to Winnipeg from Atlanta.
Professional
During pre-season to the 2011–12 season, in Scheifele's first NHL exhibition game, he scored two goals and two assists in a game against the Columbus Blue Jackets, garnering the first star. On October 3, 2011, the Jets announced that they had signed Scheifele to an entry-level contract, and that he would start the season on Winnipeg's NHL roster. He scored his first NHL goal on October 19, 2011, against James Reimer of the Toronto Maple Leafs. On October 23, he was sent back to the OHL and rejoined the Barrie Colts. After the Colts were eliminated from the OHL playoff race, he changed his number from 45 to 55 and was called-up by the Jets to play for their American Hockey League affiliate, the St. John's IceCaps for the 2012 Calder Cup playoffs. Scheifele participated in the Jets' training camp ahead of the 2012–13 season, and played with the team, however he was eventually sent back down to Barrie. For the 2013–14 season, Scheifele played in all 60 of Winnipeg's regular season games up to the NHL break for the 2014 Winter Olympics. During the season, he cemented his role as a top-six forward centering the Jets' second line, emerging as a top candidate for the Calder Memorial Trophy as the NHL's rookie of the year. However, on March 4, 2014, in a game against the New York Islanders, Scheifele suffered a knee injury that forced him to miss the remainder of the regular season. During the 2015–16 season, Scheifele surpassed the 20-goal mark for the first time in his professional career, scoring his first NHL hat-trick in a game against the Montreal Canadiens on March 5, 2016.