After barely squeaking into the Chase for the Championship in 2012 and 2013, Jeff Gordon began the 2014 season determined not to leave his fate up to the final race before the Chase. NASCAR revamped the Chase format where a victory would lock a driver into the Chase. In addition, there would be three rounds of the Chase before a championship race to end the season. Gordon began Daytona Speedweeks with a grinding crash in the Sprint Unlimited where he was caught in the wrong place when Matt Kenseth and Joey Logano got together. A 2nd place finish in the Duel gave him a solid starting spot for the season-opening Daytona 500. After a lengthy rain delay, Gordon gave Dale Earnhardt Jr the winning push at the end of the event. Gordon followed his 4th place finish at Daytona with a 5th place effort at Phoenix. It was the first time he started a season with back-to-back top-5 finishes since 1997. It was merely a prelude of better finishes on the horizon.

Gordon progressed through Las Vegas and Bristol with finishes of 9th and 7th, respectively. Ironically, it was a 13th place finish at Auto Club Speedway that thrust Gordon among the early favorites for the championship. Gordon had the dominant car on longer runs and took the race lead when Jimmie Johnson experienced a tire problem with 6 laps to go. However, a caution flag with 2 laps to go brought pit stops and a final dash to the finish. Gordon struggled on the restart and posted his first finish of the season outside the top-10. After a 12th place finish at Martinsville, Gordon came to Texas in the maroon Texas A&M Engineering/Axalta Chevrolet. Gordon started 12th and ran in the top-10 for the balance of the race. He was running 6th when a late race caution brought the leaders to pit road. Crew chief Alan Gustafson called for 2 tires and Gordon emerged with the race lead. However, Joey Logano passed Gordon coming to the white flag to relegate him to a 2nd place finish. Nevertheless, the runner-up finish gave Gordon the NASCAR points lead for the first time since 2009. The following week at Darlington, Gordon ran in the top-10 for the entire event before finishing 7th. At Richmond, Gordon led 173 laps and finished in 2nd place. He had the dominant car on longer runs, but a series of late-race restarts sealed his fate for the night. A crash at Talladega to begin May was merely a bump in the road as Gordon began heating up for the late spring and summer races.

Gordon scored his first victory of the season under the lights at Kansas Speedway. He took the race lead during a green flag pit stop sequence with 30 laps to go and held off Kevin Harvick for his 89th career win. A crash in the All-Star Race and a 7th place effort in the Coca-Cola 600 took Gordon into June with the points lead. Handling issues hindered his effort at Dover (15th), and restart issues plagued him a week later at Pocono (8th). He led the balance of laps in the first half of the race at Michigan en route to a 6th place finish. On the road course in Sonoma, Gordon's 15th place starting spot made the day more about race traffic. He came on late in the event to challenge Carl Edwards for the win before finishing in 2nd place. He closed June with a 6th place finish at Kentucky after battling back from a pit road miscue.

Gordon began July with a 12th place finish in the Coke Zero 400 at Daytona. Rain postponed the event to the following day where Gordon sustained damage after swerving to avoid Ricky Stenhouse. At Loudon, Gordon started 11th and steadily progressed through the field. The crew gambled on fuel, which came up 3 laps short. The disappointment of a 26th place finish lingered through the final off-weekend of the season. When Gordon arrived in Indianapolis, he came on a mission for his 5th career win at the famed track. Gordon led 40 laps and took the race lead for the final time from Kasey Kahne on a restart with 18 laps to go. The following week at Pocono, Gordon looked like he would make it back-to-back wins. He led 63 laps, but a late four-tire change put him in race traffic. A 6th place finish at Pocono was followed by a pole-winning effort at Watkins Glen. However, Gordon lost power during the race and needed repairs behind the wall. Once again, he rebounded after a poor finish (34th) with a stirring victory. Gordon claimed the pole and the win at Michigan using the same chassis that he used to score the win at Indianapolis. Middling finishes at Bristol (16th after a pit road mistake) and Atlanta (17th after a cut tire) brought Gordon into September.

Gordon finished 2nd at Richmond to Brad Keselowski and began the 2014 Chase for the Championship with another runner-up finish behind Keselowski. The following weekend, Gordon cut a tire while running 6th late in the race at Loudon and finished 26th. Suddenly, his Chase standing was in peril to advance to the Contender round. He made a loud statement about his championship hopes by scoring the victory at Dover. He took the race lead from Keselowski on lap 306 and was never seriously challenged. The Contender round began with a 14th place finish at Kansas. Gordon's car was never the same after he brushed the wall on lap 70 following contact from Jamie McMurray. He started and finished 2nd at Charlotte to give him an 18-point cushion heading to Talladega before the next Chase cutoff. At Talladega, Gordon started in the rear of the field and ran conservatively deep in the field for the balance of the race. Coming to the checkered flag, Gordon was essentially outside the Chase cutoff because of Kasey Kahne's standing in 7th place. However, Kahne chose the wrong drafting line in the tri-oval and slipped out of the top-10. Kahne's ill-advised move allowed Gordon to sneak into the Eliminator round of the Chase by a mere 3 points.

At Martinsville, Gordon led the mid-stages, but a pit road speeding penalty put him back in 30th place. He regrouped to move back into the top-5 and challenged Dale Earnhardt Jr for the victory. However, Gordon was unable to get to Earnhardt Jr's bumper in the closing laps and finished in 2nd place. He came to Texas feeling confident about his team's chances after a runner-up finish at the track in the spring. Gordon started on the outside of the front row and led briefly in the mid-stages. With 30 laps to go, charged from 10th place up to 2nd place with 10 to go. He took the race lead from Jimmie Johnson with 9 to go. Gordon pulled away prior to a caution flag with 4 laps to go. He chose the outside line for the restart, which essentially threw his championship hopes into chaos. Heading into turn 1, Gordon and Johnson separated and left a gap between them. Brad Keselowski, on fresher tires, positioned his car between the two Hendrick Motorsports drivers. Gordon took an arc into turn 1 and Keselowski remained in the throttle to make it three-wide. Keselowski and Gordon made contact, which cut down Gordon's left rear tire. A subsequent spin by Gordon brought out the caution flag. Gordon lost a valuable lap on pit road while the tires were changed. He finished the race in 29th place. Following the event, he exited his car and grabbed Keselowski on pit road, which incited a melee between the pit crews. Three members of Gordon's team were suspended for the rest of the season for their actions in the pit road altercation.

At Phoenix, Gordon knew that a victory would punch his ticket to the Championship race at Homestead. As the laps wound down, he found himself in 2nd place behind Kevin Harvick. He was ahead of the points cutoff when he took the checkered flag. However, in turn four, Ryan Newman moved ahead of Kyle Larson to take 11th place. The finish allowed Newman to grab the final Chase transfer spot by a single point over Gordon. In an instant, Gordon's quest for a championship had ended before he even arrived in South Florida. At Homestead, Gordon dominated the event by leading 161 laps. However, drivers on fresher tires later in the event forced Gordon to come to pit road. He concluded the season with a 10th place finish. Gordon finished 6th in the points standings for the second consecutive season. But, unlike 2013, after scoring the most total points during the season, Gordon was simply a victim of the game.

In his own words on pediatric cancer
"You see these kids like we have at our bowling tournament who have gone through the process and are now in the next stage of their lives, as healthy as you can ask for. So it pulls at you, but it's all about balance. It's the success stories that keep you wanting to do more, and give you hope that what you're doing is making a difference. But if they're all successful, then you think, oh, we can move on. And you can't move on, because there are still things that need to be done, and lives that are still being lost." - Jeff Gordon