There is definitely a story going on here! The style puts me in mind of the Terry Pratchett covers. I'm new to this too, never entered a contest like this and I'm also new to cg in general, but my only worry on your drawing is that it might be too busy? I think the guidelines recommended only one extra figure besides the champion. I could be wrong on that, but maybe someone else with more experience could give better advice.
This is great. I love the woman's expression in the latest one, like, 'how the heck did I get up here?!' Your grey scale & line work is enviable.
As a first timer to CG, I'm on a pretty steep learning curve. I've got a lot of work to do. With my horrid lack of self assuradness, it's taking a long time. Hopefully I'll have something not crappy to present at the end of February!