Cracknell played junior hockey for the Kootenay Ice in the Western Hockey League and was a member of the team in 2004–05 when it won the WHL regular season championship. During the 2005–06, his last with Kootenay, Cracknell lead the team in goals, assists, and points ; finished second in the WHL in total points; and was named to the WHL West Second All-Star Team.
Noticed by professional scouts for his size and work ethic, Cracknell was drafted by the Calgary Flames in the final round of the 2004 draft. He played three seasons with the Flames' minor league affiliates, but failed to make the jump into the NHL, and on July 16, 2009 the St. Louis Blues signed him as an unrestricted free agent. . Cracknell spent the majority of the 2011 season playing for the Blues affiliate, the Peoria Rivermen of the American Hockey League. The Blues recalled him on March 1, 2011, and on March 12, Cracknell scored his first NHL goal in a game against the Detroit Red Wings. On April 17, 2014, Cracknell scored his first Stanley Cup Playoff goal in Game 1 of the Western Conference Quarter Finals against the Chicago Blackhawks, a series the Blues lost in six games.
On July 1, 2014, Cracknell signed a one-year deal as a free agent with the defending Stanley Cup champion Los Angeles Kings. However, during training camp Cracknell failed to impress the Kings, who placed him on waivers. The Columbus Blue Jackets claimed him on October 7. Cracknell appeared in 17 games for the Blue Jackets, recording one assist. Cracknell also appeared in 18 games for the Blue Jackets' AHL affiliate, the Springfield Falcons, and recorded three goals and seven points.
Return to St. Louis
On February 26, 2015, Cracknell was reacquired by the Blues in exchange for future considerations. Cracknell spent the remainder of the season with the Wolves.
Vancouver Canucks
On August 25, 2015, the Vancouver Canucks signed Cracknell as a free agent to a one-year, two-way contract. Expected to begin the year with the Utica Comets, Cracknell impressed at training camp and was named to the Canucks' opening night roster for the 2015–16 season. On October 12, 2015 he scored his first goal for the Canucks. Cracknell appeared in a career-high 44 games in Vancouver before he was placed on waivers and claimed by the Edmonton Oilers on February 29, 2016.
Dallas Stars
On July 3, 2016, Cracknell moved again, signing as a free agent with the Dallas Stars on a one-year, two-way contract. In his first game with the Stars, Cracknell recorded 2 points with a goal and an assist. On March 24, 2017, Cracknell scored his first career hat trick in a 6–1 win against the San Jose Sharks.
Cracknell played in single game with the Stars to start the 2017–18 season, before he was placed on waivers. On October 9, 2017, his tenure with the Stars ended as the New York Rangers claimed Cracknell off waivers. After playing four games with the Rangers, Cracknell was placed on waivers on October 24 and later reassigned to AHL affiliate, the Hartford Wolf Pack.
Cracknell appeared in 15 games with the Wolf Pack before he was traded to the Montreal Canadiens in exchange for Peter Holland on November 30, 2017. Cracknell was immediately assigned to the Canadiens' AHL affiliate, the Laval Rocket and played out the remainder of the season, contributing with 27 goals and 48 points in 52 games.
On July 1, 2018, Cracknell as a free agent agreed to a one-year, $650,000 contract with the Toronto Maple Leafs. In the ensuing 2018–19 season, Cracknell appeared in 14 games and posted 10 points with AHL affiliate, the Toronto Marlies before he was traded by the Maple Leafs to the Anaheim Ducks in exchange for Steven Oleksy on December 10, 2018.
After spending his first 13 professional seasons in North America, Cracknell left the NHL and signed his first contract abroad in agreeing to a one-year contract with Chinese club, Kunlun Red Star of the KHL, on July 4, 2019.
