The most recent example that has everyone talking took place in Super Bowl XLIX between the Patriots and the Seahawks.
The Seahawks, near the goal line and trailing by four, had an opportunity to run the ball in for what would have likely been the winning score.
But with everyone expecting coach Pete Carroll to run a play for Marshawn Lynch, he instead opted to have quarterback Russell Wilson throw a short pass to the end zone that was picked off to secure a victory for the Patriots.
With that moment fresh in our minds, here's a look at other coaches, players, and even referees who have made huge mistakes at the worst possible times.-
Touchdown missing key ingredient
Kaelin Clay's mishap became a candidate for play of the year in late 2014, but for all the wrong reasons.
In a game against Oregon, the Utah wide receiver appeared to be in the clear for a touchdown. However, he forgot one fairly important detail as he crossed into the endzone.
Clay let go of the ball before crossing the line.
So instead of completing a 78-yard play for a score that would have given Utah a 13-0 advantage, the ball was recovered and run the other way for a 99 yard return.
It shifted the momentum drastically as Oregon stormed to a 51-27 victory.-
Baker's dozen not appreciated
In the 2009 Grey Cup, the Saskatchewan Roughriders appeared to be done for, leading by two points with no time left on the clock, and the Montreal Alouettes were in position to put the game away with a field goal.
Shockingly, the field goal was kicked wide and recovered by the Roughriders, who believed they had just become champions.
Slight problem, though. Saskatchewan had a 13th man on the field, and were flagged for too many men.
Montreal was given another opportunity to kick the field goal and the second time was a charm.-
Fraser forges his legacy
Referee Kerry Fraser is best known to Leafs fans for an epic non-call back in 1993.
Toronto was leading the Los Angeles Kings 3-2 in the conference final and had just scored a crucial goal to force an extra period.
In overtime, Doug Gilmour was left bleeding after a high stick from Wayne Gretzky.
A call would have yielded a penalty on the Great One or even ejection, but as Fraser admitted to the Toronto Sun 20 years later, he didn't see the play.
Gretzky scored the winner in overtime and then led his team to victory in Game 7.-
Not so fabulous
The ending to the 1993 NCAA men's basketball final between the Michigan Wolverines and North Carolina Tar Heels had a famous blunder.
Chris Webber, one of the Wolverines' stars known as the Fab Five, grabbed a defensive rebound with 19 seconds left and a two-point deficit.
The amazing thing is that the blunder Webber made shouldn't have even been allowed to happen, but after getting away with a blatant travelling violation, he advanced the ball up court and then called a timeout.
Seems like the right thing to do, except his team was out of timeouts. Michigan was assessed a technical foul, resulting in free throws and possession of the ball for the Tar Heels, who were able to ice the victory.