Wickens was born in Guelph, Ontario, and is the son of Tim and Lisa. He has an older brother, Trevor, who operated the Hamilton-based kart racing team Prime Powerteam. Wickens was fascinated by the movie Days of Thunder as a child.
Wickens began his karting career in 2001, achieving wins in the Junior Heavy Marigold Fall Classic and the Junior Lite Iron Man Enduro. He secured three championships in the Sunoco Ron Fellows Karting Championship between 2002 and 2005, competing in various classes. He also won races in ASN Canadian National Formula Junior, SKUSA ProMoto Tour, BeaveRun, PA, 80cc Junior OKRA Grand National, and Junior Heavy Mosport Grand Prix.
In 2005, at the age of sixteen, Wickens began his formula racing career in Formula BMW USA for Team Apex Racing USA, thanks to a Junior Scholarship from BMW. He achieved five podiums, including two wins, which earned him third place in the championship and the best rookie's title. He also competed in the Formula BMW World Final, finishing sixth. In 2006, he remained in the series with the same team but switched to EuroInternational after becoming a Red Bull Junior Team driver, ultimately winning the championship with three wins and seven podiums.
Wickens moved to the Champ Car Atlantic series for Red Bull/Team Forsythe in 2007, securing one win and three podiums, finishing third in the season standings. In 2008, he competed in both Formula Renault 3.5 Series with Carlin Motorsport and Formula 3 Euro Series with Signature-Plus. He claimed a win at Silverstone) in Formula Renault 3.5, finishing twelfth overall with 55 points. In Formula 3, he won at both the Norisring and Bugatti Circuit, though both wins were awarded half points due to insufficient distance covered.
In 2009, Wickens was the only North American driver in the revamped FIA Formula Two Championship, driving car number 12. He won both opening races, leading the championship, but struggled with reliability later in the season, ultimately finishing as runner-up to Andy Soucek by 51 points despite five retirements. In 2010, he raced in the GP3 Series with Status Grand Prix, achieving third place in Barcelona qualifying and leading the driver's standings after the first two races.
Wickens was crowned the champion of the Formula Renault 3.5 Series in 2011, edging out teammate Jean-Éric Vergne at the final race. In June 2011, he was signed by Virgin Racing as their official reserve driver, undertaking straight line testing and participating in the first free practice session at the 2011 Abu Dhabi Grand Prix.
On August 19, 2018, during the 2018 ABC Supply 500 at Pocono Raceway, Wickens was involved in a violent crash. After a restart, he made contact with Ryan Hunter-Reay, launching his car over Hunter-Reay's machine and into the catchfencing. The crash resulted in fractures to his legs, spine, right forearm, and a pulmonary contusion. Subsequent scans revealed an indeterminate spinal injury, and he was later diagnosed as a paraplegic. Despite the severity of his injuries, Wickens expressed hope for recovery, noting that his spinal cord was bruised rather than severed and that he had experienced some feeling and movement in his legs.
Following the Pocono crash, Wickens underwent multiple surgeries and rehabilitation. By November 2018, he published a video demonstrating his ability to walk a few steps with machine assistance. In January 2019, he showcased his progress by riding a spin bike without assistance. He drove the pace car at the 2019 Honda Indy Toronto using hand controls. During the COVID-19 pandemic, he competed in the INDYCAR iRacing Challenge and the 24 Hours of Le Mans Virtual. On May 5, 2021, he tested a Hyundai Veloster N TCR with Bryan Herta Autosport, equipped with hand controls.
In 2022, Wickens returned to full-time racing in the Michelin Pilot Challenge with Bryan Herta Autosport, driving a Hyundai car with adapted hand controls in the TCR category. He won the TCR drivers' championship in 2023 alongside Harry Gottsacker, securing wins at Watkins Glen International and Canadian Tire Motorsport Park. In 2024, he was involved in an accident during the Nürburgring Langstrecken-Serie, requiring precautionary observation in a hospital.
Wickens was awarded Indianapolis 500 Rookie of the Year honors in 2018 after leading two laps and finishing ninth. He also earned the 2018 IndyCar Rookie of the Year award despite missing the final three races of the season due to his injuries. He and Harry Gottsacker were crowned the 2023 Michelin Pilot Challenge TCR champions.
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