Worst all-time NCAA tournament bad beats

Derrick Rose (and teammate Chris Douglas-Roberts) missed key free throws down the stretch in the 2008 national title game against Kansas. Joe Murphy/Getty Images

People love betting on the NCAA tournament, which provides more chaos than any other sporting event. That has, however, resulted in agony for bettors throughout the history of March Madness.

Here is a run through the worst "bad beats" in each round.

2012 First Four

No. 14 Iona Gaels vs No. 14 BYU Cougars Closing line: BYU -2

You couldn't have asked for a better start if you took Iona as a small underdog in this 2012 First Four game. The Gaels looked like they might drop 100 points on BYU, as they had 55 points at halftime and led by as many as 25 in the first half.

The second half, well, was a different story. Iona was held to just 17 points, including a scoreless drought of over nine minutes. BYU took advantage, fueled by a 17-0 run. The Cougars completed the comeback -- the largest in NCAA tournament history -- and won by six, covering the two-point spread.

Final score: BYU 78, Iona 72 (BYU covers)

2006 Round of 64

No. 13 Pacific Tigers vs No. 4 Boston College Eagles Closing line: Boston College -8

Forget covering the spread. Pacific looked poised to pull the first shocker of the 2006 NCAA tournament.

With his team trailing by three in the final seconds of regulation, Pacific's Christian Maraker hit a 3-pointer to tie it and extend the game. The Tigers carried that momentum into overtime, jumping out to a six-point lead. But they couldn't close out Boston College, which rallied back to force a second overtime. From there, it was all downhill for Pacific, which was outscored 14-2 in the final five minutes. Simply a brutal loss if you took the underdogs to cover.

Final score: Boston College 88, Pacific 76 in two overtimes (Boston College covers)

1986 Round of 32

Arkansas-Little Rock Trojans vs NC State Wolfpack Closing line: NC State -8.5

Twenty years earlier, a double-overtime game between Arkansas-Little Rock and NC State followed a similar script to that Pacific-Boston College game.

The Trojans were seeking a second upset win in three days; they shocked Notre Dame as 17.5-point underdogs in the Round of 64. In overtime, the Cinderella team from Little Rock looked like it might reach the second weekend, as it led NC State by five. But the 14-seed Trojans ran out of gas, allowing the Wolfpack to force a second overtime, and were eventually done in by a 14-0 NC State run. Arkansas-Little Rock went from a possible trip to the Sweet 16 to the losing end of one of the worst bad beats we've seen in tournament history.

Final score: NC State 80, Arkansas-Little Rock 66 in two overtimes (NC State covers)

2013 Sweet 16

No. 4 Michigan Wolverines vs No. 1 Kansas Jayhawks Closing line: Kansas -2

It's safe to say that anyone who bet Kansas in this 2013 Sweet 16 game isn't a huge fan of Trey Burke. The top-seeded Jayhawks were in control throughout, as they looked to easily cover the two-point spread.

But Burke rallied Michigan back from down 11 with less than four minutes to play, forcing overtime on a 30-footer in the final seconds. He continued to knock down big shots in overtime, leading the Wolverines to the improbable win/cover.

Final score: Michigan 87, Kansas 85 (Michigan covers)

2000 Elite Eight

No. 2 Iowa State Cyclones vs No. 1 Michigan State Spartans Closing line: Michigan State -5

In one of the more bizarre games you will ever see, Iowa State and its head coach, Larry Eustachy, imploded down the stretch.

With just over five minutes left, the Cyclones led Michigan State by seven and at the very least were in great shape to cover the five-point spread. But as the Spartans rallied, the pressure got to the underdogs. Eustachy became increasingly upset with the officials, eventually going on a tirade that got him tossed with 9.9 seconds left. Thanks to all those technical free throws, Michigan State ended the game on a 23-5 run, sending those who bet Iowa State into a Eustachy-esque fury.

Final score: Michigan State 75, Iowa State 64 (Michigan State covers)

2004 Final Four

No. 2 Connecticut Huskies vs No. 1 Duke Blue Devils Closing line: Connecticut -2

This is probably the most well-known bad beat in college basketball history. In what felt like the de facto national championship game (no offense to Oklahoma State and Georgia Tech, which played in the other semifinal), Connecticut rallied down the stretch, sealing the victory on an Emeka Okafor free throw to go up four with 3.2 seconds left.

But the game was far from over in Vegas sportsbooks. Duke's Chris Duhon banked in a running 3-pointer at the buzzer to crush those who bet UConn. It ended as a one-point win for the Huskies but was an excruciating loss if you had them minus-2.

Final score: Connecticut 79, Duke 78 (Duke covers)

2008 National Championship

No. 1 Kansas Jayhawks vs No. 1 Memphis Tigers Closing line: Memphis -2

Missed free throws for Memphis down the stretch of this memorable title game proved to be costly for those who bet the Tigers.

After trailing by five at halftime, Memphis took control in the second half and led by nine with less than two minutes left. But Chris Douglas-Roberts and Derrick Rose combined to go 1-for-5 from the free throw line in the final 75 seconds, opening the door for Mario Chalmers' heroics. Chalmers hit a game-tying 3-pointer with 2.1 seconds left to force overtime, where it would all fall apart for Memphis. Including the overtime period, the Tigers were outscored 24-8 in the final seven minutes.

Final score: Kansas 75, Memphis 68 in OT (Kansas covers)