[4] He attended Notre Dame College in Wilcox, Saskatchewan, in eighth grade and played AAA hockey for the Hounds.

He frequently violated the school's code of conduct and was given three suspensions from the hockey team within a 16-month period, resulting in him being dropped.

[1][7] Darling said even at the lowest point, after being cut from what might have been the worst team in organized hockey, he never forgot something his father told him about getting ahead: "It was kind of like his motto—'Saw the wood that's in front of you.'

[13] On November 1, 2014, it was announced Darling had been reassigned to the Blackhawks' AHL affiliate, the Rockford IceHogs, following starting goaltender Corey Crawford's recovery from an upper-body injury.

[17] On April 15, 2015, Darling recorded his first playoff win after replacing Crawford in net, making 42 saves, with the Blackhawks defeating the Nashville Predators 4–3 in double overtime.

[19] On April 28, 2017, at the conclusion of the Blackhawks season in 2016–17, Darling's rights as a pending free agent were traded to the Carolina Hurricanes in exchange for the Ottawa Senators' original third-round pick in the 2017 NHL Entry Draft.

[23] On February 10, 2019, Darling was granted a "personal leave of absence" from the Charlotte Checkers and the Hurricanes organization for an undetermined period of time.

[28] As a free agent, Darling returned from Austria and agreed to a professional tryout contract to attend the Florida Panthers training camp on January 2, 2021.

[29] With the Panthers under the leadership of former Chicago Blackhawks coach Joel Quenneville, Darling was subsequently released without a contract at the conclusion of camp.

On January 26, Darling returned to the roots of his past success in joining the Blackhawks, signing a professional tryout contract (PTO) with the Rockford IceHogs of the AHL, to begin the 2020–21 season.

"[33] Darling played for the United States in the 2018 IIHF World Championship, mainly serving as the backup to Keith Kinkaid.

[35] Darling played in the Wayne Gretzky Ice Hockey Classic for Team USA in the summer of 2016 in Australia.