@Shade: Please see my linked screenshot above. It is not only possible, but fairly easy on any server of any population with a 25-man raid group prior to the start of any Wintergrasp battle regardless of faction.

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You know what? I'm going to be a jerk about this. Many people put a lot of time and effort into this, and it's BS that invalid entries were not only considered, but won the contest.

The winners for the 25-man Creative Headset giveaway posted on 12/04/2009 on WoW.com are, in fact, invalid based on the criteria given in the official rules. Please take immediate and appropriate action to either:

1) Provide correct, valid, complete, and timestamped (due to the passage of the submission date) entries from the winning party or
2) Issue a retraction and conduct another random drawing among the remaining qualifying submissions in accordance with the original published contest rules and regulations.

The criteria the winning entry screenshots failed to meet includes:

1) "What your guild/raid will need to do is a) get your guild or raid together, all 25 members. And then b) go and find all the places and take screenshots of your guild there (you can hit "Print Screen" to save a screenshot, and it shows up in the "Screenshots" folder of your WoW install)." (from original post) Twenty-five raid members are not visible in multiple screenshots, in particular the image at Thunderfall but in others, as well.
2) "Only entries with the correct screenshots will be included in the random drawing." According to the winner announcement, the correct screenshot for 1. was: "It's the Titan Relic you have to capture in Wintergrasp, inside the innermost room of the fortress" The Titan Relic is not visible in this image.