This term is used to connote positivity, or negativity with a particular situation, or object.

On its own, the term is good. But, mix up your words a bit, and you can flip it around to make it seem bad.
"Dude I crashed into a manure truck the other day."
"I'm not surprised, your driving isn't exactly award winning."

"That Klipspringer is an award winning son of a bitch."

"Dude, Terry is so rico suave with the ladies, it's award winning."
by Raney November 19, 2004
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A turd so incredible that it merits formal recognition.
There is absolutely no doubt that this was an award winning turd!
by Dr Bunnygirl November 19, 2019
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When your favored underdog sports team achieves a 0-0 result.

This is a play on the: "Darwin Award."

Wikipedia states: "The Darwin Awards are a tongue-in-cheek honor originating in Usenet newsgroup discussions around 1985. They recognize individuals who have supposedly contributed to human evolution by selecting themselves out of the gene pool by dying or becoming sterilized via their own actions."

If further reference is required, you my friend, have just achieved your own Darwin Award...!
Scotland Football League won the Draw-Win Award against England. Yes!
by Rebdiculous June 19, 2021
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