The Prize Was The Best Parking Space For His Horse

I like to think that back in feudal times, some king handed out a “Sentry Of The Century” award

This would assume the fact that back in feudal times, they actually had awards ceremonies.  I think the rampant celebration of doing a good job is a relatively recent phenomenon.  

I would agree, but at the same time, we don't really have sentries anymore.  Sure, there are security guards and whatnot all over the place, but I don't think they're called "sentries."  It's a little sad, really.

Also, back in feudal times, if you were a good sentry, that usually means that you were still alive after the castle was attacked.  Being a bad sentry probably meant you were dead.  Also a little sad.  

But great motivation for being good at your job!  

So whether or not some knight of the realm was presented with the title "Sentry Of The Century," I prefer to think that it happened.  You can choose to believe it or not...but it's certainly more fun if you do.