Lol, who cares about the winning entry/ies?
Let's see, ah, shiik just got to mind. He deleted his icons, and yes, the ones where he got best of 3 in Icon Contest #9 are included.
Reputation/award icons are enough, nobody will see the entries except they go look for them. Like what happened to the UI's of Text. Contest #18. Only one contestant uploaded his resource in the respective section, the others might aswell not exist.
You get the idea?
Also, I'd like to read a rule that explicitly forbids deleting them. Otherwise I see no reason not to do that afterwards.