Check out the updated main post
I added volt's excellent archival work, reversing the order so the oldest shows up at the top and standardizing the link format for most of them. I didn't want to mess with Denton's cool post too much, so his formatting is the same except for me putting the links within the challenge title and putting the Cursed Challenge in there with some font-color finesse. Then I added my post from the first page to constitute the New Era, which so far has averaged 9 challenges per year! (18 over about a 2 year span)
There were a few notable oddities - due to a tie in one challenge, Captain_Nemo was able to win two challenges in a row without hosting in between. Possibly even more unique, puma_03 won two challenges but never hosted any. But here's the real kicker - Nemo had a bizarre pattern: hosted a challenge, then won 4 without hosting in between, and then hosted 2 more. Obviously things weren't as consistent back then, but it's still a funny thing to see.
With my usual affinity for a little bit of number crunching, we've listed 46 fleet challenges in this thread so far. Volt and I are tied at the top of the leaderboard with 6 wins apiece - I ranked volt higher because my latest win was rather unimpressive and he faced higher numbers of entries in some of his earlier wins, compared to me losing fleet challenges when I submitted a whopping 3 entries.
However, a win's a win, and since we joined at basically the same time, I calculated that we've each won about 17% of the challenges that have been hosted since we joined, so combined we make up about a third of the wins since mid-2011 (12/35). However, longevity obviously plays a big role, and between the number of past users who have left the site and the current users who haven't participated in all of the challenges, it's only common sensical that the most consistent participants would have the most challenge wins.
For the leaderboard I put active members ahead of non-active, with ties being decided by recent activity. I'd still like to go back and find any other old challenges to make this 100% complete. If anyone is ever extremely bored and has a ton of time on their hands, feel free to figure out how many people submitted X fleets per challenge (similar to Denton's format), and from there how many fleets they've submitted overall, win percentages based on wins divided by # of challenges entered, etc, etc.