The Detroit Tigers fly on DC-9 N682RW owned by Mike Ilitch, who owns both the Tigers and the Red Wings. The aircraft is painted in both teams' colors, and there are a few repaints around for download. I believe the Red Wings get priority until the end of the NHL playoffs.
I've been hoping to see some of these flights in the bid division for a while now!
http://flightaware.com/live/flight/N682RWEdit>> Whoops, just saw on flightsim.com only an AI repaint is available for download. Will have to check AVSIM when I get home (blocked at work).