Someone in a progressive league with a DH did it by accident with Mike Hampton, he had Hampton playing the outfield.
I don't know what his settings were, but my guess is there were no OFs available in the player hierarchies because guys were fatigued, so the SIM picked the best option available, which happened to be great-hitting pitcher Mike Hampton. So you have to set up your rest hierarchies such that the SIM runs out of position player options and needs to turn to pitchers, but it will probably only work if the pitcher is a better hitter than anyone else available.