Race Weekend Central

The 10: The Biggest “Should Have Won” Races of the Past 25 Years

This week, the teams of the Monster Energy NASCAR Cup Series enjoyed their final weekend off until the season ends. Whether it was traveling the world or relaxing at home, the competitors did whatever they felt would recharge their batteries. So I decided to give our contributors a chance to clear their minds as well. Which group needed the break more? I suppose that’s all a matter of perspective.

Regardless, this week we present to you something that sports fans in general are all too familiar with: the dreaded near miss. Not winning is always tough but when a sure win is exchanged for bitter defeat, it can almost chip away at one’s soul. NASCAR is chock full of examples of this indiscriminate gut punch. But what are the worst?

Due to the abundance of such occurrences throughout the sport’s history, I’ll limit this to the past 25 years. Otherwise, the list would have probably taken a year to put together. So here are ten times that I thought a driver “shoulda had that one” in a Cup race. What are yours?

How the Rankings Are Calculated: Ordinarily, Frontstretch does our power rankings similar to how the Associated Press does them for basketball or football. Our expert stable of NASCAR writers, both on staff and from other major publications, will vote for the top 10 on a 10-9-8-7… 3-2-1 basis, giving 10 points to their first-place driver, nine for second and so on. In the end, Frank Velat calculates the points, adds some funny one-liners and… there you go! But this week, he kicked everyone out and took the whole thing over. Anyways, have a look.

Total Votes


Juan Pablo Montoya: 2009 at Indianapolis

Montoya was without question the best car at Indy that weekend. It wasn’t just that he led 116 of the first 124 laps. He would shoot out to huge leads and just keep getting further away. Then he was busted for speeding on pit road and had to serve his penalty. Montoya nearly became the only driver to win at Indianapolis in both IndyCar and NASCAR.



Brad Keselowski: 2010 at Texas

There were 334 laps in this race. Keselowski led 312 of them. It’s almost ludicrous to think he wouldn’t win, but a debris caution with 18 to go brought the field close and Jimmie Johnson tracked him down and got by with four to go.



(Photo: NASCAR)

Kyle Busch : 2009 at Daytona

Busch was on his way to a Daytona 500 triumph when things got a little too aggressive on the backstretch. Maybe you feel he blocked Dale Earnhardt Jr or you think Earnhardt turned Busch. Either way, the 88 laps Busch led meant nothing when his car sat wrecked in the Turn 3 infield.



(Photo: NASCAR)

Tony Stewart & Kurt Busch: 2007 Daytona 500

The only two cars that could touch each other during the first three-quarters of the race ended up doing just that. Contact left both in the Turn 4 wall and added to the Daytona 500 frustration for both. Busch exorcised his demons this year but Stewart retired having never won the big race.



Marcos Ambrose: 2010 At Sonoma

Trying to save fuel a little too aggressively ended up costing the Aussie a shot at his first career win. While leading under yellow, Ambrose turned off the engine and wasn’t able to cut it back on until after five cars, including eventual race winner Jimmie Johnson, had passed him by.




Rusty Wallace: 1999 Daytona 500

Like Stewart, Wallace finished out his career without a Daytona 500 trophy. This race was no doubt his best shot, as he led 107 of the 200 laps. But a banzai move by Jeff Gordon with 10 laps to go switched Wallace’s fate with that of Gordon, who would pick up his second 500 victory.




Hut Stricklin: 1996 at Darlington

While Stricklin wasn’t as dominant as some on this list, he did lead the most laps. The heartbreak in his run at Darlington Raceway was in the fact that he never even came close to winning after this race. The runner up finish to Jeff Gordon was the last top-five finish of his career.



Bill Elliott: 2003 at Homestead

2001 winner Elliott led 189 of the 267 laps and appeared to have his 44th career in hand. Until he cut a tire on the last lap. Elliott never won another Cup race.




(Photo: NASCAR)

Martin Truex Jr: 2015 at Dover

For the second week in a row, Truex led 191 laps. For the second week in a row, he didn’t win. Don’t feel too bad though. He wound up in Victory Lane the following race at Pocono.



Matt Kenseth: 2013 at Martinsville

Kenseth had a great shot to win at what has statistically been his worst track. Leading 202 laps wasn’t enough though, as Jeff Gordon chased him down and got past with 20 to go, relegating Kenseth to second.



Who Voted: Frank Velat, Frontstretch

About the author

Frank Velat has been an avid follower of NASCAR and other motorsports for over 20 years. He brings a blend of passionate fan and objective author to his work. Frank offers unique perspectives that everyone can relate to, remembering the sport's past all the while embracing its future. Follow along with @FrankVelat on Twitter.

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The “banzai move by Jeff Gordon” brought the double yellow line into existence. I call it the Jeff Gordon rule.


I think there is a typo on number 2. That Texas race Brad dominated was 2015.

Nik Joans

How is it that not one of MANY crushing last lap defeats of Dale Earnhardt Sr at the Daytona 500 did not make at least one spot on the list. Leading easily on the last lap and cutting a tire, allowing Derrick Cope to win. That is just the most obvious choice.


That was 27 years ago, out of the time line.


When there is a Biggest “Glad He Won” article, would Kyle Busch be a possibility?

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