OT: Best (or Worst) Sports Wager You Ever Made

[Wheels Of Steel]

With the start of football still months away, and in the spirit of the “biggest concert regret” thread which generated some fun (and sometimes wistful) reminiscences, I thought the perhaps we could do something similar with tales of our best (or worst) sports bets.


Here’s my contribution: In 1990 I was living in West Lafayette, but I had travelled up to Madison for a visit. One night just before bar-time, one of my buddies announced that, having just hired Barry Alvarez, Wisconsin was going to the Rose Bowl within 5 years. Now, Wisconsin hadn’t been to the Rose Bowl in almost 30 years, and hadn’t even had a winning season since 1984. I pointed out that with Penn State entering the conference, and Michigan and Ohio State still around, a trip to Pasadena for Bucky seemed unlikely.


The fact that both of us might have been overserved gave rise to the following bet: If Wisconsin did, indeed, get to the Rose Bowl in five years, I would pay for airfare for two, Rose Parade Tickets, game tickets, and lodging. Otherwise, he would foot the bill for two for a week in Cozumel.


Well, needless to say, as soon as Wisconsin clinched a trip to the Rose Bowl 4 seasons later, my phone rang, and all I said was “Send me the bill.” Ended up costing me about $4K. One of the student newspapers there in Madison interviewed me and ran a story about the whole episode – incredulous that someone would pay off a 4-year old, bar-time, sports wager. For several years thereafter (until Purdue finally made the trip in 2001), I used to say that “I’ve never been to the Rose Bowl, but my money has.”


Best sports bet I ever made.


Oh, and I did win back three dollars from that same friend by beating him in three games of Nerf basketball a couple of years later.

 

[BoilerBulldog]

At the Bellagio sports book several years ago for NFL wildcard weekend with buddies. Great time. The Redskins game I bet a bunch of random prop bets and right before halftime Evan Royster caught a TD pass, pulling it in through a pile of players. He stood up with the ball and that single play won three different bets for me. Royster was something like 50-1 to score, I won the halftime spread, and I think something to do with the over under. I netted something like $750. Put my whole weekend in the black. I was the only guy in the entire room going nuts over Evan Freakin' Royster.

 

[TopSecretBoiler]

1997 Arizona over Kentucky was a good one.
Picking Denver over Balitmore in the playoffs when they lost on that last second bomb (WTF to this day). I had to eat cinnabon for lunch for a week and they got to choose my meal. omg...
My worst is probably yet to come as I will take McGregor over Mayweather.

 

[Wolegib]

with my long history of losing sports bets, I bet against the Purdue Women's basketball team. and bet they would lose the NCAA championship game. and thanks to me, they won.

 

[JohnnyDoeBoiler]

1997 Arizona over Kentucky was a good one.
Picking Denver over Balitmore in the playoffs when they lost on that last second bomb (WTF to this day). I had to eat cinnabon for lunch for a week and they got to choose my meal. omg...
My worst is probably yet to come as I will take McGregor over Mayweather.

I will also take McGregor over Mayweather because unlike most of the guys Mayweather has fought, McGregor has legit stopping power in his left from literally anywhere and he'll be athletic enough to follow Mayweather's antics of floating around the ring. I wouldn't put it past McGregor to get deep under Mayweather's skin and get him to stand in front and actually fight. Boxing is a lot less taxing than MMA .

 

[housedaddy72]

April 2005, I did as my wife had asked and put $10 down on the White Sox to win the World Series at 30:1.

 

[ahhculdee]

I said RG3 would bust in the NFL from injuries. Last year I said Carson Wentz would be better than Goff.

 

[nat100]

Best - i bet two hundred on Florida Gulf Coast to beat GTown at +350 (that was a hell of a weekend in Vegas after that game)
Worst - I bet the Bengals would beat the Texans in the playoffs the year Yates was the starter. Dalton is the worst.

 

[jsglenn4]

I boxed three 1994 college bowl games.

Tennessee (-7) to cover against Virginia Tech.
Colorado (-7) to cover against Notre Dame.
Alabama (-6) to cover against Ohio State.

They seemed like locks to me and the Vols and Buffs easily covered. However, Bama and OSU were tied at 17 very late in the game with the Tide grinding out what would surely be the winning drive. I knew there was no way Stallings was going to risk a pass the way they were running the ball and that they would settle for the FG with so little time left on the clock. I turned off the game only to miss the screen pass Bama decided to throw. It broke down the sidelines for a touchdown and I didn't know for about an hour I had scored pretty big. However, I was so miserable worrying about the lines, I didn't enjoy a moment of any of the games. I've not placed a serious bet on a game since.

 

[JohnnyDoeBoiler]

I bet $100 (only time I have ever bet with real money) when I was a sophomore in high school. A friend of mine was a huge Titans fan and I was giving him a hard time about how much the Rams could beat the Titans most days of the week. I finally got under his skin enough for him to throw a wager with a 'put your money where your mouth is.' Needless to say I was sweating bullets until 'The Tackle' and I immediately called him (on his home phone!) and said...i'll be needing that $100 by the end of the week. He paid up on Friday! Figured I had my one win and haven't gambled on sports since!

 

[Boilerdoughnut]

I am a defensive pessimist when it comes to purdue sports so I regularly bet that Purdue will never cover the spread when favored and always lose by more than the spread If not favored. I regularly bet a cup of coffee on each game with a colleague who knows nothing about Purdue sports compared to my knowledge. However , a few years ago, at season's end, I owed him about --15cups of coffee. He graciously accepted a Purdue t-shirt and a book I had written instead of the coffees. But this past season, I lost another 13 coffees and he has refused to accept alternate payment/even though I offered him an autographed copy of the same book I gave him a few years back. The debt is still unpaid .but I have to pay up before the 2017 season kicks off.

 

[TC4THREE]

Best wager: Hit an 11 team parlay on Friday of the opening week of the NCAA tournament last year. Wasn't a cheap one either with big money line favorites. All 11 were either ATS or money line underdogs. $10 paid about $23,000.

Worst: My freshman year at Purdue in 1995 there was a guy down the hall from me that was from Chicago and all excited about Northwestern beating Notre Dame early that season. He started yapping about Northwestern being great and headed to the Rose Bowl. Up to that time, Northwestern football had generally been a joke and I figured it was just a random, fluke upset and even if they were somewhat good I didn't figure they'd win the Big Ten and go to the Rose Bowl. So my statement, without any consideration in return, was that if Northwestern went to the Rose Bowl I'd buy pizza for our hallway (probably about 10-15 rooms in Cary Quad). Fortunately, they allowed me to buy the pizzas separately and not all at once.

 

[TC4THREE]

I said RG3 would bust in the NFL from injuries. Last year I said Carson Wentz would be better than Goff.

I told my roommates in college that Tim Duncan would never be anything in the pros. To this day, I'm reminded of that constantly.

 

[Wolegib]

I told my roommates in college that Tim Duncan would never be anything in the pros. To this day, I'm reminded of that constantly.

boy were you dumb ! hen again, I was the guy who said Greg Oden was going to be the next Tim Duncan !

 

[TC4THREE]

boy were you dumb ! hen again, I was the guy who said Greg Oden was going to be the next Tim Duncan !

Well at least you can blame injuries on that one.

 

[PaBoiler78]

Well at least you can blame injuries on that one.

not a big gambler, but the one time I was in Vegas, Purdue was playing Rhode Island in the NCAA's and since I was watching it in Vegas I put $50 on us and thanks to Brian Cardinal hitting a last second shot I won too.

 

[Heiner]

Today's Preakness

 

[BoilerBulldog]

Best wager: Hit an 11 team parlay on Friday of the opening week of the NCAA tournament last year. Wasn't a cheap one either with big money line favorites. All 11 were either ATS or money line underdogs. $10 paid about $23,000.

Worst: My freshman year at Purdue in 1995 there was a guy down the hall from me that was from Chicago and all excited about Northwestern beating Notre Dame early that season. He started yapping about Northwestern being great and headed to the Rose Bowl. Up to that time, Northwestern football had generally been a joke and I figured it was just a random, fluke upset and even if they were somewhat good I didn't figure they'd win the Big Ten and go to the Rose Bowl. So my statement, without any consideration in return, was that if Northwestern went to the Rose Bowl I'd buy pizza for our hallway (probably about 10-15 rooms in Cary Quad). Fortunately, they allowed me to buy the pizzas separately and not all at once.

Very nice! $10 for $23K? Impressive. What did you do with the money?

 

[TC4THREE]

Very nice! $10 for $23K? Impressive. What did you do with the money?

Nothing too exciting. Some went to savings. Most went to mortgage.

 

[Bullwhip Griffith]

Nothing too exciting. Some went to savings. Most went to mortgage.

Mortgage being the name of his favorite stripper

 

[PU52Chevy]

Have two that stand out:

I bet $25 for Cubs to win the World Series every year in Las Vegas (Golden Nugget) from 1997 to 2004 (odds were usually 90 to 1) and they never won it...pissed money away and then go figure they win last year.

I know nothing about Nascar but had tickets to the inaugural Las Vegas 500 race and put $20 on Jeff Burton (Liked the purple and black color of his car) to win it and sure as shit he won......won like $280 and treated the whole group I was with to beers at the Yardhouse all night.

I never bet on Purdue....ever.

 

[ossim]

I bet on Cincy to beat Dallas in the superbowl with my dad when I was a child for a lifetime's worth of lawnmowing. Still paying it off in my mid 30's today.

 

[Wheels Of Steel]

I bet on Cincy to beat Dallas in the superbowl with my dad when I was a child for a lifetime's worth of lawnmowing. Still paying it off in my mid 30's today.

Great story, ossim - reminds me of a time when I was a kid, and shooting marbles was popular at recess. I had acquired probably 30 or so marbles, mostly aggies and catseyes, plus a couple of shooters. anyway, I asked my dad one day if he wanted to play, and he said he'd play if I lent him a shooter, and we played for keeps. Within 10 minutes all of my marbles were gone.

 

[sluggo69]

1983 gave my buddies the boilers and 45 1/2 vs. the Irish. My first ever game in Ross-Ade was quite enjoyable.