Before the days of the Pinstripe Bowl, there was the Kickoff Classic played at giants stadium. The Hawkeyes played in the game twice in 1987 and 1992. Like this year's team, many of the players had never been to the Big Apple before those trips.
The culture shock was almost immediate when Columbus Junction native and Iowa tight end Craig Clark arrived to play in the 1987 contest.
"Boy you get off the plane in New York City and there's a lot of people everywhere," Clark said. "In Iowa, you could look around and step outside and see a tree. You get in New York City and there's just people and buildings and cement and concrete. I remember feeling like being outside and still feeling clausterphobic, just because the buildings were so tall it seemed like you were inside."
The Hawkeyes did have a few players from around New York City, including receiver Quinn Early. The memories of playing near home sticks with him 30 years later.
"It was an amazing experience being there with my teammates," Early said. "Got to see a lot of friends and family. We played the Tennessee Volunteers. I remember it like it was yesterday."
The heartbreak of a last-second, game-winning Tennessee field goal is tough to forget.
Still, Early said playing in a nationally featured game was an incredible moment for a college kid.
"All eyes were on us and it was just... it was phenomenal and I feel fortunate to have been able to play in a game like that," Early said.
Five years later, Jim Hartlieb led the Hawkeyes into the 1992 classic against N.C. State.
"I was kind of an unproven quarterback, so I had a lot of butterflies around how am I gonna perform on the big stage," Hartlieb said.
The Hawkeyes lost to the Wolfpack 24-14, but it was a moment away from Giants Stadium that Hartlieb still cherishes today.
"We had an offensive lineman, Mike Ferroni, who was from Union, New Jersey," Hartlieb said. "We had a little bit of time the next day to be able to go to his hometown and see his family and they had a big spread for us. To be able to go to their backyard was pretty special."
The former Hawks all believe the team will have a fantastic experience in New York City. They hope it includes a win at the Pinstripe Bowl and Yankee Stadium.
"For the guys that haven't been there before and maybe are from small-town Iowa, small-town Illinois like I was, it'll set you back a little bit, but they'll grind past that and get to work, I'm positive of that," Hartlieb said.
"You just have to stay focused and not get distracted by the pagentry of the whole thing," Early said. "Especially for the guys that are there for the first time. The main focus is on that game...and winning it."
If the Hawkeyes do get the victory, it will be their first in a bowl game since 2010. It might take away the sting of those Kickoff Classic losses too.