Have you ever entered a contest?

I got a$500 grant in middle school for photography. I slay raffles.

I once won a five pound Hershey bar at a store.

Won a 5k race in ROTC out of like 100 ppl

If by contest you mean buy X product and see if you win a prize. Then yes.

It was a single k cup coffee dispenser. And it was from a box of special K. Honestly I didnt even check until I was breaking down the box for recycling.

If we are talking about talent shows then no.

Yes. I entered a contest on a Facebook group where you had to say some funny anecdote and the funniest gets a custom mug delivered to them. I entered it with a funny memory about how I met Dan Wright (the guy who plays Little cook) at my cousin's wedding when I was 10, and I said to him that he was a lot bigger in real life than he was on the telly, and I won and I got the mug which had a picture of my choice on it, which I still have and I'm having a cup of tea in it as I am writing this.
I also came 3rd place in a fancy dress costume in college, I was dressed as Wonder woman, and I won a cinema gift card thing (which I never got to use) and a watch. I also got a "special" rosette when I was in a contest in college where we had to dress up our horses, and although we came 4th, our theme was marvel or superheroes so I dressed up in the wonder woman costume again (nobody else really bothered to dress up) and I was freezing out there cause it was kind of a skimpy outfit, and I got the special rosette because I made the effort to dress up and even though it was freezing.
I have also won contests on Animal Jam, including fashion shows, and a guest speaker thing in a livestream, and wheel giveaways. One of my favourite ones was in a talent show on Animal jam, and I decided to be MJ, and so I dressed my penguin up as him and sang/typed the lyrics to "ABC 123". And I won the talent show and I got some prize Icr.

I once entered a Mii contest and came dead last I ranked 50th place out of 50 people in the world.

Honestly 50th place was better than not winning. I took it as a big victory.

As a kid, I did a baking contest (got blue and red ribbons) and a few art contests, one of which I won. I also came third or fourth (can't remember) in the spelling bee in fourth grade! I also took place in horse and rider Halloween costume contests at a couple of the barns I rode at as a kid, and won one or two of those. My horses were saints to put up with the crap I made them wear! 🤣

I showed horses, mainly hunters and equitation, throughout my childhood and adolescence as well, and won or placed well in many. I also played the violin in high school and scored well at state as a freshman.

A few years back, I entered a contest to win a free horse bit, thinking "I probably won't win, but hey, why not enter just for the sake of it?" and surprisingly won one! I still have it, though I've never had a chance to use it, as that was not long before I got out of horses. I never would've dreamed I'd have actually been one of the winners! Hopefully I'll get a chance to actually use it someday.

i won a spellin bee in junior high school and got pretty far in the state competition

I won a pee sword fighting contest with my brother.

Yes.

Won 1st place at a local car meet in Bulgaria once for best car condition.
The prize was a bottle of wine, or something like that. It was 11 years ago.

Nope.

i won a few writing/story contests in school and a contest my fashion design class held where you had to redesign like a shirt/pants

I once won 341st place in national football tipping. I was so proud to be 1st of the 340’s

I entered a writing scholarship and received a decent amount of funding for my entry. I suppose those sorts of scholarships are *technically* contests.

I've won 4 gold/2 silver/1 bronze medals in submission wrestling.