This year’s Daytona 500 victory wasn’t the first long-awaited triumph in Michael McDowell’s career. Five years ago, the 36-year-old veteran landed another eagerly anticipated win at the site of this weekend’s Cup Series event — Road America.

RELATED: Road America weekend schedule | Cup Series standings

That 2016 Xfinity Series breakthrough ended a drought of nearly 300 NASCAR national-series races for McDowell, who cashed in on a spot start with Richard Childress Racing. He’d come close before at the 4.048-mile road course, qualifying in the top five for each of his Xfinity starts there, but misfortune seemed to follow him. Nearly five years ago, all the pieces aligned.

“My fondest memory was just coming off the final corner there and knowing that I had it, just a relief,” McDowell says, noting strong performances in his previous efforts there with Joe Gibbs Racing. “Just so many things had gone wrong there where I’d led a lot of laps there, had some opportunities to close the deal there and just wasn’t able to do it. So to finally do it, it was just a big sense of relief and accomplishment.”

Wisconsin is a heck of a place for an Arizona native to have a homecoming, but no matter the geographical contrast, McDowell is ready for a reunion on friendly turf in America’s Dairyland. He’ll bring a heaping helping of experience into Sunday’s Jockey Made in America 250 presented by Kwik Trip (2:30 p.m. ET, NBC, NBC Sports App, MRN, SiriusXM NASCAR Radio), the first Cup Series event at the Elkhart Lake facility since 1956.

McDowell’s winning ways at Road America extend beyond his handful of Xfinity Series starts. He also won there twice as he established his road-racing chops in the open-wheel Pro Mazda Series, prevailing for the first time in 2003 and again the following year on the way to the series championship in the Road to Indy program.

Advantage, McDowell? That might be the case in terms of experience at the long, high-speed circuit, but the Front Row Motorsports driver acknowledged that the rest of the Cup Series field is a quick study.

“I think it’s always an advantage to have experience, especially good experience where I’ve been in quality cars and had great runs,” McDowell says, “so I think that kind of experience is helpful, but … the drivers are so talented and the tools that we all have with simulation and videos and data, you have a fairly good idea of what you’re going to do and how you’re going to do it before you ever get to the race track. The great guys are going to figure it out fast. I’d actually prefer it if there was no practice because I think when you give talented people that 50 minutes, they’re going to figure it out and you might lose some of that advantage you might have.

“At the same time, I wouldn’t give up the experience. I think it always helps.”

MORE: McDowell wins Road America in 2016

Another helpful asset: McDowell’s already banked season-opening win, which has virtually assured him a playoff berth and the highest finish in the Cup Series standings for his career. It’s been a handy insurance policy for the postseason, but winning the “Great American Race” has also magnified McDowell’s stature.

Since the start of the season, McDowell has appeared in national ad campaigns for CarParts.com, and just last weekend at Pocono, the team added sponsorship from new backer Horizon Hobby and its ARRMA RC brand for his No. 34 Ford. “I think that winning the 500 and just having a solid year in general has been so helpful with our relationships here at Front Row,” he said. “Anytime you run good and your partners are happy, it creates opportunity.”

It hasn’t hurt McDowell being introduced with “Daytona 500 winner” as a prefix to his name.

“I don’t know if you ever get used to it, but it’s nice,” McDowell said. “This sport is so challenging and it’s week to week, and you’re only as good as your last race. So when you have a struggle and a difficult weekend, and you come to the office to do autograph requests or sign pictures, when you keep signing that same picture of you in Victory Lane at the Daytona 500, it’s a good reminder that when you’re struggling, it’s worth it.”

The struggles have been less frequent this year, with McDowell already posting career-best numbers with five top-10 results and a 16.8 average finish. For McDowell, those stats and the win-column check mark haven’t spurred any thoughts about testing the free-agency market. While he says those positives haven’t necessarily accelerated any negotiations with Front Row in an already busy Silly Season, McDowell has indicated that he expects to stay put.

“It’s pretty early for us, but I’ve kind of said this before: I plan on being here. I enjoy the growth that we’ve had at Front Row and what we’ve been able to build,” McDowell says. “To go from when I got here, running high 20s to 30s every week to running low 20s to running in the teens, then winning a race and being in the playoffs and having more top 10s and top fives than we’ve ever had, it’s a fun time to be a part of Front Row. I’m enjoying being here and hopefully that’ll be an opportunity for years to come, but we haven’t really gotten to that point yet.”

Firming up plans for 2022 can become a priority later, but McDowell & Co. have work remaining for this season. Seven events remain before the 10-race playoffs begin, and McDowell says that FRM is striving to make gains on the more well-heeled teams in the Cup Series garage.

“We’re still a small team and we still have a budget, but we are able to build a few new cars and have some time to work on those cars and make them the best that we can before the playoffs start,” McDowell says, “but we also look at these next three or four weeks as big weeks for us, having three road courses coming up and knowing that those are races that we can contend in.

“You’ve got to balance your focus. Obviously, you don’t want to get too far ahead, but you also want to make sure you’re prepared for the playoffs. We’re doing everything that we can.”