Additional features to a Wordpress website - repost

We need to add a function to send out a "loser" email to selected entrants - i.e. there will be a list of entrants per day as requested - then for that day, we need to be able to select one as a winner, and then send a loser email to all the other [login to view URL] for example - every morning there will be a number of entrants for the previous day. We need to be able to mark one as a winner (which is fine if its something as simple as deselecting) - and then send all the others a generic "loser" email.