Fucking a chick in the ass while going down a waterslide.
Steve and Mindy were kicked out of Waterville for performing a back-alley bobsled.
by ahrnygoose September 23, 2010
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A term used to describe a situation that is possible, but unlikely to happen. Popularized by the tv show Glee.

Based on the 1988 Winter Olympics team who fell short of winning any medals but did surprisingly well.
"What do you think the chances are that Jennifer will say yes if I ask her to go out with me?"

"Jamaican Bobsled Team, dude..."
by P Banger February 15, 2010
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v.
similar to a tobagon

the act of four black guys gangbanging a chick on top of a staircase and then riding her down.
The hooker asked, "Would you negros care for a jamaican bobsled team?"
by yea bro August 9, 2007
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While hooking up with a chick, drop a huge log on her chest and then titty fuck her with it
Oh man so I was watching Cool Runnings with my girl and I asked her if she's ever been introduced to the Jamaican Bobsled Team, she replied no, so I went ahead and fulfilled her wildest dreams.
by blimRU February 10, 2011
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The act of shitting a REALLY long turd. So long it starts wrapping around itself in the bowl.
That was one hell of a ride on the baby ruth bobsled!
by jamaican babyruth bobsled team September 7, 2008
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Pop-culture phrase loudly exclaimed after one (or a group) achieves something which the person or group was unsure of completing. To be sung in a forced Jamaican accent, see ja-fake-an
by Kung-Fu Jesus April 28, 2004
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When you’re out of town with your boys and there’s no hotel hot tub, so you pile in the room’s bathtub instead.
“How was your trip?”
It was fun! The place didn’t have a hot tub, so we went bobsledding instead”
by PCThiker2650 January 26, 2019
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