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A tape measure will help you with any "bolt-on" issues,,(I'm guessing no problem there) but the wiring harness and location of it will be different. You might have to do some custom work to be sure the wiring stay's away from the tire
Other than wiring for your lights, yes. It will bolt right up. This is kind of odd, most of us with the newer style street bobs are getting rid of the chopped fender to go to the fender you have. I literally have an '06-'08 fender sitting on my dining table right now. Waiting for a couple more parts to get in. Good news for you, you'll be able to sell your old fender for a pretty penny. If its still in good condition that is.
Are you wanting to keep the side mount plate and signal location as is on a '15 FXDB?
As far as "custom work for wiring"....no. See part labeled as 20/24. Ask your buddy if he's going to give this to you or not. The fender bracket mount (20/24?) have plastic pieces the kind of snap on and hold the wires between the fender and the plastic. Really quite simple.
I'm doing this now. 2006 to a 2015. Signals are already LED mini mounted to frame and the tail light and plate are going to a side mount. The clean look is better in my opinion.
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