What if Gollum won the riddle game?

[Ingwë]

Ingwë, do you really think Bilbo could beat Gollum in a fight, given how Tolkien portrayed both of them up to that point?

Yes, I think. He has a sword - The Sting. Жилото. He could kill Gollum.

Gollum, on the other hand, was able to throttle goblins who happened to wander into his territory.

Gollum is strong, but he kill goblins while he is using the Ring. But Bilbo have found the One Ring. Gollum doesn`t possessthe Ring. He is visible. Bilbo may become invisible (destiny).