I'll answered based on the general consensus via the given feedback as well as my own.
There are not enough people that would actually want this to happen in order for it to work. The Showdown lobby has only recently seen consistent activity and that's starting to go down again. There are not enough people that care to make it work as well as we want it.
As I said before, its more hassle than it's worth. It's more effort and more time spent than any actual enjoyment you could probably get out of it.
We've tried actual DB leagues in the past and they don't last very long due to the userbase getting bored of them quite quickly, and as a result they've become defunct. And this is when we had more competitive battlers on the site compared to casual users.
Even if we were to just manually keep track of points, it just feels like a big waste of time when only a few people would ever actually use the system. If you want to prove yourself as a battler here, then we have scheduled tournaments, or you could just challenge people. Many of us would say yes.
Bring this up again when the userbase grows more, then we'll reconsider.