In 2014, Ware competed in the Lamborghini Super Trofero North America series, winning Rookie of the Year honors. In 2019, Rick Ware Racing formed an Asian Le Mans Series program with Ware and Mark Kvamme as drivers of the Ligier JS P2. In their first race at Shanghai International Circuit, despite missing qualifying and only having two laps of practice, Ware and Kvamme finished second in the LMPS Am class and 14th overall. On November 23, Ware announced he would compete in the 2020 24 Hours of Le Mans for EuroInternational. In January 2020's Asian Le Mans race at The Bend Motorsport Park, Ware and co-driver Gustas Grinbergas finished fifth overall and recorded the LMP2 Am Trophy class win.
In August 2014, he made his debut in the NASCAR Nationwide Series at the Mid-Ohio Sports Car Course, starting 26th and finishing 15th. Ware was scheduled to race at the Xfinity Series' Phoenix race in November, driving the No. 13 for MBM Motorsports, but his flight was delayed causing him to miss the race and later replaced by Rubén Pardo.
In 2015, Ware joined MAKE Motorsports full-time for the 2015 NASCAR Camping World Truck Series season, competing for Rookie of the Year honors. However, on May 1, Ware announced that he would be leaving the team to attend college full-time, with aspirations for a pre-medical degree. Ware was replaced by Travis Kvapil in the No. 50. Ware returned to the Truck Series in 2017, driving the No. 12 for RWR on a part-time basis.
In June 2016, Ware attempted to make his Sprint Cup Series debut in the Toyota/Save Mart 350 at Sonoma Raceway, driving the No. 55 for Premium Motorsports, but he failed to qualify. He joined RWR's Cup Series program, driving the No. 51 part-time in 2017. He made his Cup debut in the Folds of Honor QuikTrip 500 at Atlanta, driving the No. 51 with sponsorship from Spoonful of Music and Bubba Burger. Ware started and finished 39th, retiring from the race on lap 74 with steering problems. At Dover and Pocono, Ware's No. 51 acquired sponsorship from East Carolina University and Clemson University, respectively, with the latter also featuring logos celebrating the football team's 2017 College Football Playoff National Championship win earlier in the year. During the Dover race, Ware withdrew from the event after 283 of 406 laps after suffering from back pain. A week later at Pocono, he left the race after completing 35 laps, again for back problems. He was scheduled to drive at Michigan but Ware decided to stay out of the car for the race and the team didn't find a replacement driver in time. He returned to the No. 51 for Darlington's Bojangles' Southern 500, where he drove a car painted like Tom Cruise character Cole Trickle's Mello Yello vehicle of the same number in the film Days of Thunder; Ware's No. 51 featured logos saying "Pray for Texas", with RWR producing merchandise of the car and donating all proceeds to Hurricane Harvey relief efforts. On lap 157, Ware was involved in a wreck with Matt DiBenedetto and A. J. Allmendinger; after the race, Ware and DiBenedetto argued on Twitter over responsibility for the wreck. When DiBenedetto faulted Ware for the incident, the latter replied by falsely accusing him of infidelity, causing a firestorm that led to Ware deleting his social media for the rest of the season and up through 2018. A few months later, in February 2018, Ware restarted his Facebook profile and announced his Asperger's diagnosis in May. Ware later revealed in a January 2019 interview that the incident with DiBenedetto was one of his "biggest setbacks ever," but acknowledged "hitting rock bottom was the best thing that happened to me because that really gave me the wake-up call of 'hey, this is only going to get worse, and you're never going to come back from it unless you do something about it right now.'" In 2018, Ware transitioned to motorcycle racing, though he made sporadic Truck and Xfinity Series starts for Mike Harmon Racing, while also returning to the Cup Series for RWR at Dover and Sonoma Raceway, where he would DNF and place last.
Season still in progress Ineligible for series points Ware began the 2018 season racing for Truck Series points but switched to Cup Series points before the race at Sonoma. Ware began the 2019 season racing for Cup Series points but switched to Xfinity Series points before the race at Talladega.
