10. November 6, 1993 Wisconsin 14 Ohio State 14
The first Buckeyes game I remember watching, this one hurts more because my dad was so upset. As it turns out, he was right to be so angry; the tie (along with the annual John Cooper loss to Michigan) cost the Buckeyes an outright Big Ten title, and instead of going to the Rose Bowl, they beat BYU in the Holiday Bowl. My introduction to Ohio State disappointment was complete.
9. November 22, 2003 Michigan 35 Ohio State 21
The Buckeyes and Wolverines each had only one loss, and a win would have given the Buckeyes the Big Ten title and a Rose Bowl berth. In hindsight, this hurts a whole lot less, since it's the last time Michigan beat Ohio State.
8. November 7, 1998 Michigan State 37 Ohio State 13
Ohio State went into this game ranked #1 (as they had been the entire season) and absolutely loaded (David Boston, Antoine Winfield, Andy Katzenmoyer, among others). While the loss cost the Buckeyes a shot at the national championship, most fans were certain Ohio State would lose to Michigan, anyway (a game the Buckeyes of course won).
7. October 11, 2003 Wisconsin 17 Ohio State 10
Coming off their shocking upset of Miami in that January's Fiesta Bowl, Ohio State was looking to repeat as national champions. Unfortunately, they ran into the Badgers and Chris Chambers in prime time. The sting would have been greater from this one if the Bucks hadn't just won the national title.
6. November 23, 1996 Michigan 13 Ohio State 9
Despite losing Terry Glenn, Rickey Dudley, Bobby Hoying, and Heisman Trophy winner Eddie George, the Buckeyes rolled through the '96 season undefeated, only to lose to the Wolverines in the last game of the season for the second year in a row. The fact that the Buckeyes went on to beat Arizona State in the Rose Bowl makes this one hurt that much more, since the Rose Bowl victory would have given Ohio State at least a share of the national title.
5. January 5, 2009 Texas 24 Ohio State 21
After getting blitzed in the previous two national championship games and earlier that season by USC, the Buckeyes were looking to redeem their national reputation with a win over the heavily favored Longhorns in the Fiesta Bowl. The upset appeared to be in their grasp, as the Bucks had the Horns in a 4th-and-3 with around a minute left in the game and Ohio State on top 21-17. Colt McCoy, however, hit James Kirkendoll to convert the four down, and two plays later, hit Quan Cosby for a 26-yard, game-winning touchdown.
4. November 25, 1995 Michigan 31 Ohio State 23
Ohio State was rolling through the regular season behind a high-powered offense fueled by Eddie George, Bobby Hoying, Terry Glenn, and Orlando Pace. Undefeated coming into the game, Eddie George was expected to carry the Buckeyes to victory and cement his Heisman Trophy candidacy. Instead, Wolverine halfback Tim Biakabutuka ran for 313 yards and a touchdown, and Michigan upset their rivals 31-23. George would still win the Heisman, but a deflated Bucks team would go on to lose the Citrus Bowl against Peyton Manning and the Tennessee Vols, 20-14.
3. September 12, 2009 USC 18 Ohio State 15
This one hurts for all of the same reasons losing to Texas in the Fiesta Bowl hurt. Just when it seemed the Buckeyes were going to regain some national respect, they blew it.
2. September 10, 2005 Texas 25 Ohio State 22
In one of the biggest non-conference games in memory, the Buckeyes and Longhorns traded leads until Ohio State seemed to go up for good after a field goal made it 22-16 with 5:12 left in the 3rd quarter. The Buckeyes should have scored a touchdown on the drive to make it 26-16, but tight end Ryan Hamby dropped the would-be TD catch not once, but twice. After holding Texas at bay for most of the fourth, Vince Young finally took over and led the Horns on a 7-play, 67-yard scoring drive to put Texas up 23-22 with 2:37 left. After Ohio State fumbled and got a safety to pretty much end the game, I threw a chair through my wall. I still hate Ryan Hamby.
1. January 8, 2007 Florida 41 Ohio State 14
Ouch. The game that really started America's complete disdain for the Buckeyes, you can read my thoughts on this one here (language NSFW, as I was pretty drunk when I wrote it).