I believe it went by the second giveaway's rules but the first giveaway's timer.
Code:
GA Begin Claims: Selected wilflare to win game 65FC92C0FC07DC64 17:59:28.433000 1404511168.43
GA: Claim Process: Reading posters from thread 847028 17:59:28.433000 1404511168.43
GA: Claim Process: Reading posters from thread 844556 17:59:30.373000 1404511170.37
GA: Claim Process: Poster nominally meets no-lurker requirements: wilflare -- 132 17:59:35.539000 1404511175.54
[b]GA: Claim Process: wilflare meets giver requirements. Has 7 giveaways during eligible period. 17:59:56.883000 1404511196.88[/b]
GA: Claim Process Throttle: Poster has won 4 times in last week. 17:59:56.917000 1404511196.92
GA: Claim Process Throttle: Use 900 17:59:56.920000 1404511196.92
GA: Claim Process Throttle: Poster must not have a win since 1404510296 17:59:56.923000 1404511196.92
GA: Apparent last win is 1404301180 so OK 17:59:56.956000 1404511196.96
GA: Claims Process: I am going to give Dead Rising 3 to wilflare. Added to PM Queue. 17:59:57.088000 1404511197.09
Based on that line from the log, it was the second giveaway's rules.
I believe I've figured out why the timer thing happened.
Yes, that is the cause. ModBot check eligibility (including the global throttle) when it selects you to win, not when you enter. So if you ever enter an expired raffle, win instantly, and there's more than one previous entry, those other people were ineligible.