The 10 Most Memorable March Madness Moments of All-Time

For me, nothing in sports tops March Madness. And it’s not even close.

The shocking upsets, the breakout performances, the heartbreak, the joy, the Cinderella stories, the passion.  All of it.

As I get further into my 30s, there are plenty of things I don’t remember too well, but the number of vivid memories I have of the NCAA Tournament is extensive to say the least.  Consequently, the task of putting together the Top 10 March Madness Moments proved to be a challenging yet enjoyable trip down memory lane.

Keith Smart hits the game-winning shot for Indiana in the 1987 NCAA Championship game against Syracuse. Where will it fall in Andy's list of the top 10 March Madness moments of all-time?

Before I get to the list, after a brief discussion with some of the other writers from Midwest Sports Fans, I defined a “moment” more as an individual play.

So for example, Texas Western’s win over Kentucky in 1966 had tremendous historical and social significance, but it isn’t on this list because no one play from that game stands out as iconic.  Same with Magic vs. Bird in 1979.  The overall significance to that game to basketball in general is off the charts, but there isn’t a singular moment that is replayed each year at tournament time.

(Don’t worry though. We’ll be counting down the top 10 March Madness moments – “Impact Edition” – in a later post. And we already have our March Madness 2012 Quick Preview up for your edification.)

The best thing about a list like this is the debate that ensues, so I would love to hear your thoughts on what I missed or what you would include based on its importance to you as a sports fan.  On with the list…

10. Gordon Hayward missing from halfcourt

Let the vitriol flow!

Yes, I included a shot that didn’t even go in, but it was the culmination of a magical tournament run by Butler where they were inches away from winning the title…on a halfcourt shot…in their hometown.

Here is a unique angle on the shot you may not have seen:


The Bulldogs came into the game on a 25-game winning streak, and they gave a favored Duke team all they could handle throughout the game, which featured seven ties and 15 lead changes.  Neither team ever led by more than six points.

Hayward had just missed a jumper that would have given the Bulldogs a one-point lead in the closing seconds, which led to Butler fouling Duke’s Brian Zoubek with 3.6 seconds remaining.  He made the first and missed the second, which Hayward grabbed and turned toward halfcourt.  Butler’s Matt Howard obliterated Kyle Singler with a screen to give Hayward a glimmer of space, and the shot nearly banked in but clanged off the rim.

If that shot goes in, it’s likely number one on this list.

9. Bo Kimble shooting free throws left-handed

Even as I write this, I get goosebumps thinking about Kimble’s tribute to fallen teammate Hank Gathers.

A heart condition caused Gathers to collapse and die on the floor during the Semifinals of the 1990 West Coast Conference Tournament.  The event was eventually canceled, and Loyola Marymount was awarded the automatic bid by virtue of having won the regular season title.

The team had made headlines all season for their uptempo style of play, led by the “Guru of Go” Paul Westhead.  That season the Lions scored over 122 points per game, which not surprisingly led the country.

Kimble and Gathers were the two stars of the team and close friends off the floor, with Kimble finishing as the nation’s leading scorer at 35.3 points per game.  To honor his teammate, Kimble vowed to shoot his first free throw of each NCAA Tournament game left-handed.


Interestingly enough, Gathers was actually right-handed, but his struggles at the stripe led him to begin using his off-hand on free throws at one point in his career.  Kimble was outstanding in the tournament and led the Lions to the Elite Eight.

He was also perfect on left-handed free throws.

8. Bryce Drew knocking out Ole Miss

With the 13th-seeded Crusaders down by two points in their first round matchup against the Rebels, Ole Miss star Ansu Sesay went to the line for two shots with 4.1 seconds left.  But he missed both, and Valparaiso eventually wound up with the ball on the baseline with just 2.5 seconds to play, leading to one of the most exciting finishes in tournament history.


“Pacer” was the play, and the Crusaders executed it flawlessly with Jamie Sykes throwing a perfect pass to Bill Jenkins, who was able to catch it and direct it to a streaking Bryce Drew, who nailed the game-winning three-pointer as time expired.

The ensuing celebration featured a cool father-son moment between Bryce, and his dad, Homer, the team’s head coach.

Click to continue and see the G.O.A.T. give us a preview of his greatness and the two most inexplicable late-game decisions March Madness has ever produced.

About the Author

Andy Bottoms

While Andy was born and raised in Indiana, he would like to point out that he grew up shooting hoops in his driveway and not against the side of a barn like you see in all the March Madness promos or in the middle of a field like Jimmy Chitwood. Andy ranks among the top bracketologists according to the Bracket Matrix and has provided his projections to Fox Sports for the past three seasons. When not compiling excuses for missing work during the NCAA Tournament, Andy enjoys spending time with his wife and two daughters. He is a proud IU graduate and co-hosts The Assembly Call postgame show following every IU game. Twitter: @AndyBottoms