1. Northwestern 2008: jNWU 22, Iowa 17
This is the obvious choice for the worst loss in Iowa history, mainly because nobody could see it coming. Ricky Stanzi had the case of the turnoversies that he usually saves for cupcake opponents like A-State, Indiana, and jNWU.
But even with a expulsion-worthy helmet-to-helmet hit incapacitating Shonn Greene by Brad Phillips and Stanzi's full smorgasbord of new and creative changes of possession, Iowa still had a 1st and goal inside the jNWU 10-yard line with time running out. Alas, the four plays called failed--obviously because O'Keefe was O'Throwing the O'Football game--and Northwestern walked away with college football's most stunning upset of 2008.
Karma rewarded Northwestern when lowly Missouri ran them out of the stadium in the Alamo Bowl later that year, while Iowa cruised against the far superior South Carolina.
2. Northwestern 2005: jNWU 28, Iowa 27
The sight of Kyle Schlicher pushing the field goal that would have made the game 30-14 late in the 4th quarter haunts us to this day. What ensued was an epic meltdown, with Iowa giving up a quick touchdown, an onside kick, and another quick touchdown.
Did the pain end there? No no, friends; no no. Drew Tate got the Hawkeyes moving after the fatal touchdown and had the ball inside Northwestern territory with under 30 seconds to play; two passes bouncing off Herb Grigsby's hands later, we all tried to kill ourselves.3. Northwestern 1999: jNWU 23, Iowa 21
Some people may think of this as not being much of an upset, being that 1999 Iowa was the school's single worst team in the past 35 years, and Northwestern didn't win until a touchdown on the game's final play. Well, yeah, that's why this is #3 on the list of worst Iowa upsets of all time and not #1.
4. Northwestern 1990: Iowa 56, jNWU 14
Just Northwestern fought gallantly for upwards of four minutes (real time, not game time; that'd be ridiculous). Alas, Iowa was much too tough, and God's Team prevailed again. No, the real upset here that we didn't hurt their boys too bad. That usually happens.
5. Tulsa 1996: Tulsa 27, Iowa 20
AAAAGH AAAAGH AAAAGH AAAAGH KILL THIS MEMORY DEAD WITH A FLAMETHROWER. But it's not as bad as only beating jNWU by 42. They're just Northwestern.