Lally began in karting, earning two WKA National Gold Cup Championships, before entering sports car racing in 1993 through SCCA regional events. In 1997, he won the US Formula 2000 Rookie of the Year award in his first full professional single-seater season. From 2004 onward, he built his reputation as a specialist road racer in the Grand-Am Rolex Sports Car Series, winning at least one race in each of eight consecutive seasons from 2004 through 2011 — a streak unprecedented in the series. In May 2010, he became only the second driver in Grand-Am history to complete one hundred starts, marking the milestone with a win at Virginia International Raceway.
Lally became the all-time leader in GT class wins, podiums, and top-five finishes in the Grand-Am Rolex Sports Car Series. He is a three-time Grand-Am Rolex Series Champion. His record across the Rolex 24 at Daytona is particularly notable: he recorded five class victories at the event, which tied him for fourth on the all-time Daytona 24 Hours win list. His first Daytona GT class win came in 2011 with Magnus Racing, and he added his fourth win in that class in January 2012, co-driving a Magnus Racing Porsche 911 GT3 Cup with Richard Lietz, René Rast, and team owner John Potter. His fifth Daytona class win followed in 2016 with Magnus Racing in the GTD division.
In May 2012, Lally became the first driver in Grand-Am history to record one hundred podium finishes, reaching the milestone at New Jersey Motorsports Park.
Despite his primary identity as a road racing specialist, Lally also campaigned in NASCAR, winning the 2011 NASCAR Sprint Cup Series Rookie of the Year for TRG. He made multiple partial starts in the NASCAR Xfinity Series over subsequent years, earning several top-ten finishes, including a career-best fifth place in 2017 at Mid-Ohio. In 2023, he returned to the Cup Series with Rick Ware Racing for multiple road course events — his most Cup starts since 2011.
For the 2017 IMSA SportsCar Championship season, Lally joined Michael Shank Racing to debut the Acura NSX GT3 alongside Katherine Legge. The pairing scored the first and second worldwide victories for the Acura NSX GT3, at the Detroit Grand Prix and Watkins Glen International respectively, with Lally also claiming the car's first worldwide pole position at Watkins Glen. He returned to Magnus Racing for 2018 in an Audi R8 LMS and continued with the team through subsequent seasons.
In December 2024, Lally announced he would retire from professional driving after the 2025 Rolex 24 at Daytona. His final race with Magnus Racing in an Aston Martin Vantage GT3 Evo was cut short within six hours by a mechanical retirement.
Outside motorsport, Lally holds world championship credentials in street luge, winning the 2012 IGSA World Championships in both the Street Luge and Classic Luge disciplines in Calgary, and winning the Classic Luge world title in 2009 at Bathurst. He holds a black belt in Brazilian jiu-jitsu and is a competitive mountain biker.
Immediately after his racing retirement in 2025, Lally was appointed president of the Trans Am Series, while indicating his intent to continue participating annually in the Rolex 24 as a competitor.
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