Am I being whooshed? How do you mean?
I don’t think this really counts. You play a game with rules which define the winner. In this case (and in my sailing example above) you’re saying that the person who would lose a different game is the winner in this game. Since everyone knows the rules going in, the winner of lowball poker is the winner, regardless of how their hand would fare in a completely different game. Of course, this is just semantics since it’s not really clear what the OP is after. I think Philster has the best answer so far in finding a case where the loser of a game actually wins from a broader perspective.
Tractor ‘slow races’ are a feature of many rural festivals-last man/machine over the finish line wins.
In tennis, it’s possible to win more games than your opponent but still lose the match. Example:
6-0
6-7
6-7
Depends on what you mean by “winning”. Technically, if you lose a contest, you cannot be the winner in that contest. Now, if by winning, you mean gaining some advantage in a bigger or follow-up contest, consider the way the NFL do their drafts. Teams with poorer records select first. So by losing, a team can move up on the draft. I thought of another example in MLB (baseball). Suppose Team A has already clinched a playoff spot and is playing Teams B and C that are still in the running for a spot. It’s possible for Team A to “intentionally” lose to the weaker team between B and C to help that team’s chances. Then A can possibly end up playing the weaker team in the playoffs. I’m not saying that has happened, but it’s possible.
Pool is another game where one player may not have sunk any of their balls, but the other player can loose by sinking the white ball off the blace (a strategy I have employed on many occasions).
My poker experience has always been such that when playing low-hand, straights (and flushes) don’t count. So the worst hand would be 5-high.
Of course, there are variations, and in poker you can make any rules you want. But I thought ace-to-five low-hand was pretty common (if not more common than ace-to-six)
The ancient Mayans played a game a little like basketball, where in the Captain of the *winning]/i] team was beheaded.
I’m not sure if any of these answers count. In low-hand poker, for example, you don’t win by losing. The rules by which you win are just different from what most people are used to. If the OP was clearer, it’d help.
Yup, and it’s called NCAA Football. Last year was a particularly blatant example of most of the country considering a team who didn’t win the BCS to be the true champion.
My poker experience has always been that when playing lowball, all poker hands are recognized, so that a straight or flush would count as a high hand. I’ve never seen it played with at 5-high being the lowest hand.
Actually, usually I’ve seen it played as hi-low, with the high hand and the low hand splitting the pot. I’ve only rarely seen straight lowball played.
Special Olympics.
Well, there is a new reality show called The Biggest Loser where the loser is the winner…
OK, I’ll be quiet now.
Ah, I came into this thread to post that. Too late. (Only, I was going to dub it “Xtreme Dieting.”)
Hearts, if card games can be considered sport. Goal is not to take on any hearts unless you take 'em all and the lowest score wins.
Or any card game such as I Doubt It where the object is to get rid of your cards.
The example which leaps to my mind is the boxing at the 1988 Seoul Olympics. Some of the decisions were so clearly wrong that some of the losing boxers were indeed generally acknowledged to be the winners of their bouts.
Another one. “That shadow has lingered over amateur boxing for a long time. But it exploded into the public eye during the tumultuous Seoul Olympics in 1988, which ended with Roy Jones Jr. being robbed of a gold medal against a South Korean.”
In “bracket” drag racing. This type of drag racing allows cars with all different types of modifications to race against each other. The driver enters his car into a “bracket”, that is, he declares the absolute top speed (lowest ET actually) his car will run. So when two cars meet in a race, the car that declared the slower ET gets a head start on his opponent. A car can win the race but “break out” and actually lose. A break out is when a car runs faster than his declared ET.
As an American, I know extremely little about cricket. (I do have a crisket bat, but it’s for comedic intimidation. 
) I have a book that explains cricket, and there was something in it about the importance not being which team won, but how the game was played. I think it had something to do with individual statistics. My post was only partially serious.
Russian Roulette?
There are different forms of lowball. Straight low-ball and hi-lo split exist. Typically in hi/lo split games, A-2-3-4-5 is the lowest hand.
In “regular” lowball, like “razz” (7-stud lowball) A-2-3-4-5 is the lowest hand, even if it is a flush.
In the less common, but not rare (still played at the WSOP), “deuce-to-seven” lowball, 2-3-4-5-7 is the lowest possible hand and I BELIEVE that flushes hurt you. I think that this is played in draw-poker format.
There’s a famous example of a soccer game where a team somehow advanced to a next round if they lost, but didn’t advance if they won or drew and the team was trying to score on itself at the end of the game.
But, they didn’t win the game if they lost. THey just got some side-benefit like a team getting the first draft choice.