Put a 21 inch wheel on my 12 street glide with a 120-70-21 Avon cobra, discovered my fender was rubbing ever so slightly (like the width of a piece of paper) so I drilled out the holes like Hogpro suggested on these forums,

Supposidly I should be able to get a 5/16 bolt taped to the tire, however, I can not, it literally raised the fender less than 1/8 of an inch and it still rubs, my fender is now ruined also and will need paint, and I'm going insane... What is the actual solution to this problem?

 

Drilling out ALL of the mounting holes worked for me when I had a 21 up front, no damage to my bike. Did you drill out all the wholes or just a couple of them?

 

I drilled out only the rear, and pulled the lowest point of the fender up, I need to drill all 4 and pull the *** up and press the front down to open the gap enough in the back?

 

That's what I had to do brother. I don't want you getting upset if it doesn't pan out if you drilled it more because of me and it didn't work, but we drilled out all of mine to leave for the most amount of adjustment and it was fine. If your bike is lowered you will also need to make sure you have enough clearance from above the fender to down below. We put my bike in a wheel dock and used tie straps to crank the front end down as if it would bottom out to check for clearance.

Good luck, maybe someone else can offer up better advice.