Cundiff called the miss a "tough pill to swallow." But it certainly wasn't the first setback for an Iowa kid who blossomed from a wannabe quarterback at a non-scholarship FCS school to an All-Pro kicker.
Cundiff was a three-time all-state pick as a quarterback at Harlan High, a small-school football powerhouse in western Iowa, and kicked out of necessity. Cundiff had hoped to play quarterback at Drake, but he quickly discovered his future in football was as a kicker.
Cundiff was also a point guard for the basketball team who played sparingly, though he quit before his senior season to concentrate on football. He said the relative anonymity of kicking for the Bulldogs - who rarely draw more than a few thousand fans a game - allowed him to get all his mistakes out of his system away from the spotlight.
By the time Cundiff left Drake, he held school records with 284 points and 49 career field goals.
"I like to tell people that my parents groomed me to be a basketball player, but God made me a kicker," Cundiff said.
Cundiff bounced around the NFL, spending four seasons with Dallas and one with New Orleans before finding himself out of the game in 2007.
Cundiff, who got his MBA from Arizona State, spent the next two years working for a venture capital firm. But Cleveland lured him back to the game in 2009, and he finally found a permanent home when Baltimore signed him in November 2009 after the Browns waived him.
After being cut by NFL teams nine times, Cundiff earned All-Pro honours in 2010 and doesn't have to look over his shoulder despite the biggest miss in team history.
For that, Cundiff is grateful.
"They knew if I had that same situation to play over again, I'd probably make it 99 times out of 100," he said. "It was a really strange situation. The team understood the context of it all. So they knew going forward that they don't have to worry about me, because they know what I've been through."
Cundiff half-jokingly said that expectations at his high school were so high that losing the state title game was considered by some to be a disappointing season. But Cundiff also learned a great deal about perspective while at Harlan.
Cundiff said his coach at Harlan rarely talked about winning or losing. He instead told his players to simply put forth their best effort, a lesson Cundiff leans on to this day.
"We just talked about playing the best we could and, as he'd say, let the chips fall where they may. And I think that's the attitude I've taken when I got into the NFL. I know I'm going to fail, and I know I'm going to have some success. I'm going to put my best effort out there, and sometimes it's not going to be good enough, and sometimes it's going to be more than enough," Cundiff said. "But at the end of the day, can I look myself in the mirror and say I did the best I could? If that's the case, then I know I can't really do any more than that."