They split after the 2008 season when Stewart left to become co-owner of Stewart-Haas Racing, and Stewart begins this season with his third different crew chief since Zipadelli.
It's certainly evidence Stewart has struggled to find the same chemistry he had with Zipadelli all those years. So why not just reunite with Zipadelli?
Zipadelli told The Associated Press on Friday it crossed his mind, and he even he offered last year to return to the pit box this season with Stewart.
The three-time Cup champion wouldn't entertain the idea.
"He wouldn't let me. He shot me down pretty quick," said Zipadelli, who as vice president of competition at SHR manages all four of SHR's Sprint Cup teams.
Zipadelli admitted he misses calling races and the competition side of being a crew chief—something he didn't anticipate when he left Joe Gibbs Racing after the 2011 season to move into a management role for Stewart. He still got into the action calling 10 races in 2012 for Danica Patrick, but was strictly behind the scenes all of last year.
"I miss the adrenaline. I really do," said Zipadelli, who also thinks the crew chief position has changed the last few years into "just 24/7 worry. You worry about these guys and if you did everything that we could for them.
"Back then, crew chiefing was so much more adrenaline. Ups and downs, I loved it. It's what drives you. Now it's just worry, 365 days a year. And there aren't the same highs."
But he was still willing to give it a try again with Stewart when it was decided late last season to replace Steve Addington atop the pit box.
SHR ultimately hired former Martin Truex Jr. crew chief Chad Johnston, who will get his first chance to work with Stewart on Feb. 14 when doctors are expected to clear him to drive for the first time since breaking his right leg in an August sprint car crash. His first day of practice comes a day before the exhibition Sprint Unlimited at Daytona International Speedway.
Johnston will be trying to recreate what Addington and Darian Grubb before him could not—the give-and-take relationship that Stewart and Zipadelli forged from their first day together as rookies in 1999.
"I think it's hard to have what we had," Zipadelli said. "Instantly, we learned to have mutual respect for each other. We didn't always have a like every day of our lives together, but there wasn't a day in those 10 years that I didn't feel like he didn't have my back and there wasn't one single day of his life where he didn't know I had his back. We may have argued and fought and went through a lot of crap, but at the end of the day, we both wanted the same thing and believed in each other.
"That sometimes is hard to come. He's a different person now than he was then. He's changed a lot, he's mellowed a bit. But, he needs someone to push him at times and tell him things he doesn't want to hear.