I don't think it will fit, In 05 they changed to a full double din radio, which is larger than the 99-04 SD's factory radios. I'm sure you could "make" it fit with some gentle persuasion. I don't know about wiring though. Again I'm sure you could make that work too, just depends how much effort you want to put into it. Personally, I would just get a nice aftermarket unit with all the features you're looking for. and have much better sound quality