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| 2025 | Confirmed to compete in the IMSA SportsCar Championship for Cadillac Whelen, expanding his racing portfolio. |
| 2024 | Drugovich returned to racing in the European Le Mans Series with Vector Sport, competing in an challenging season where he achieved one podium finish (third place) at the 4 Hours of Imola and ultimately finished 15th in the standings. |
| 2024 | Drugovich was confirmed to test IndyCar machinery with Chip Ganassi Racing at Barber Motorsports Park, expressing surprise at the speed of the car after the test. |
| 2024 | Competed in his first 24 Hours of Le Mans with Whelen Cadillac Racing, finishing 15th in the Hypercar class. |
| December 2024 | Drugovich participated in free practice, setting the ninth fastest time, and later completed the Abu Dhabi Pirelli tyre test with 146 laps. |
| November 2024 | Drugovich participated in the Abu Dhabi Grand Prix free practice, finishing 9th. |
| September 2024 | Drugovich completed a test at the Circuit de Barcelona-Catalunya, testing 2026 prototype tyres. |
| May 2024 | Drugovich returned with Maserati for the Berlin rookie test. |
| February 17 2024 | Inducted into the Canadian Motorsport Hall of Fame at age 37, becoming the youngest inductee in the hall's history. |
| 2023 | Became an occasional co-commentator on Channel 4's F1 coverage and F1TV feed in the United Kingdom |
| 2023 | Felipe Drugovich turned down an opportunity to test for Ed Carpenter Racing during the winter testing season after the 2023 racing season. |
| 2023 | Drugovich participated in the rookie practice session at the Rome ePrix with Maserati, topping the timesheets. |
| 2023 | Participated in the Race of Champions in Sweden, partnering with Thierry Neuville in the ROC Nations Cup for the All-Star team. They defeated Team USA and Team Germany before losing to Team Norway in the final. |
| 2023 | Continued as Reserve/Development driver for Aston Martin Aramco Cognizant F1 Team and also became Reserve driver for McLaren F1 Team |
| 2023 | Dale Earnhardt Jr. continued to race for JR Motorsports in the NASCAR season. |
| November 2023 | Drugovich drove in the first free practice session of the Abu Dhabi Grand Prix, finishing second fastest. |
| September 2023 | Drugovich tested at the Hungaroring. |
| June 2023 | Drugovich drove the AMR21 in a private test at the Red Bull Ring. |
| April 2023 | Drugovich drove for Maserati MSG Racing during the Formula E Berlin rookie test, finishing first and setting a lap time just two-tenths slower than Maximilian Günther's best time in the SABIC Berlin E-Prix. |
| April 2023 | Drugovich collected additional F1 mileage in the AMR21 around Silverstone. |
| March 2023 | Drugovich drove the Aston Martin AMR23 during the first session of pre-season testing in Bahrain, replacing injured Lance Stroll, and completed a total of 117 laps. |
| 2022 | Re-joined MP Motorsport for the Formula 2 season, partnering with Clément Novalak. |
| 2022 | Won his first pole position of the season at Jeddah, taking the championship lead for the first time. |
| 2022 | Dale Earnhardt Jr. participated in the NASCAR racing season driving for JR Motorsports, achieving 45 points. |
| 2022 | Johnny Herbert concluded his role as a pundit for Sky Sports F1. |
| November 2022 | Drugovich had his first contact with a Formula One car, testing the AMR21 at Silverstone and meeting the requirements to obtain the FIA Super Licence. |
| November 2022 | Drugovich drove in the post-season tests in Abu Dhabi with Aston Martin. |
| October 2022 | Joined the crew of F1's Weekend Warmup for United States Grand Prix, Mexico City Grand Prix, Sao Paulo Grand Prix, and Abu Dhabi Grand Prix |
| September 2022 | Sealed the 2022 FIA Formula 2 Championship title at Monza, finishing the season 101 points ahead of nearest rival Théo Pourchaire. |
| September 12 2022 | Drugovich was announced as the first member of the AMF1 Driver Development Programme and joined Aston Martin's reserve driver roster, two days after winning the 2022 Formula 2 Championship. |
| May 2022 | Became the first F2 driver to win all races in a single weekend at Barcelona, moving back into the championship lead. |
| March 2022 | Set the fastest time during pre-season testing at the Bahrain International Circuit. |
| 2021 | At Baku, involved in an incident with Oscar Piastri on the opening lap of the first sprint, resulting in a ten-second time penalty and finishing 14th. |
| 2021 | At Sochi, set the fastest time during practice but crashed heavily on the way to the starting grid, resulting in a hospital check and being declared unfit for the feature race. |
| 2021 | Joined Virtuosi Racing as a driver alongside Guanyu Zhou for the FIA Formula 2 Championship season. |
| December 2021 | At the final round in Yas Marina, finished fifth in the feature race, passed Shwartzman on the penultimate lap to secure a podium. Jumped to eighth in the championship standings with 105 points. |
| December 12 2021 | Hinchcliffe announced he would step down from racing full-time and join NBC Sports as a commentator for the IndyCar Series broadcast from the 2022 season onwards. He was replaced in the No. 29 entry by Devlin DeFrancesco. |
| May 2021 | At Monaco, qualified ninth and secured his first podium of the season by finishing second in the first sprint race. |
| March 2021 | At the Bahrain International Circuit, topped free practice and qualified third for the opening race. Finished the feature race in 8th place (later demoted due to a safety car infringement). |
| January 26 2021 | Andretti Autosport announced Hinchcliffe would drive the No. 29 car co-entered by Steinbrenner Racing full time for the 2021 season. He finished 20th in the points standings, with a best result of third at the inaugural Music City Grand Prix. |
| 2020 | Joined NBC Sports as an analyst for IndyCar and select IMSA races |
| 2020 | Hinchcliffe finished 18th at the first race of the season at Texas Motor Speedway, 11th in the Indy GP, and 7th in the Indy 500. He later replaced Zach Veach for the final three races of the season in the No. 26 car. |
| December 2020 | In the second Bahrain round, Drugovich was promoted to third place after Nikita Mazepin's penalty, concluding his rookie Formula 2 season with a total of three wins, one pole position, and four podiums. |
| November 2020 | In the first Bahrain round, Drugovich won his first feature race, overtaking pole-sitter Callum Ilott and winning by 14 seconds. |
| October 12 2020 | Earnhardt and Amy Reimann welcomed their second child, a daughter named Nicole Loraine Earnhardt. |
| August 2020 | At Barcelona, Drugovich won the sprint race by a dominant 9.5 seconds, which he described as making up for a missed opportunity in the feature race. |
| August 2020 | At Silverstone, Drugovich recorded his maiden pole position, beating Callum Ilott, though he finished seventh in the feature race. |
| July 2020 | Drugovich won his first Formula 2 race at the Red Bull Ring, leading every lap and overcoming three safety car restarts. |
| February 19 2020 | Andretti Autosport signed Hinchcliffe to a three-race deal for the 2020 season, marking his second stint with the team. He was scheduled to compete in the GMR Grand Prix, the Indianapolis 500, and the Genesys 600. |
| 2019 | During race two, suffered a puncture after contact with Robert Shwartzman while battling for third place, resulting in both drivers retiring from the race. |
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This contents of the box above is based on material from the Wikipedia articles James Hinchcliffe, Felipe Drugovich, Johnny Herbert & Dale Earnhardt Jr., which are released under the Creative Commons Attribution-ShareAlike 4.0 International License.