1. The sheriff and the deputy won since the deputy is the last one living.
2. The outlaws won since the sheriff was the next player clockwise to play his turn b/c the card is played clockwise.
3. The game is a draw since both the sheriff and the outlaw died at the same time.
I have the 10th anniversary edition of the game, I have not found anything in the rule book about cards like Indians being played clockwise, only one I know that gets played clockwise is "General Store." On the Video Game app though it shows all cards being played clockwise, but I figured its more for convenience. I welcome any explanations so I can finally put this round to the grave so to speak. Cheers.
