Will Boss 338 (18x8/18x9.5) fit on my 69 cuda?

What exact tire size and backspacing/offset doe you have front and rear?

What's the distance from the tops of you wheel lips to the ground front and rear?

I'm trying to fit 17x9 with 275/40/17 tires on very soon. I know the front bottom edge of the front fender lip needs to be moved out/cut/bent 1.5-2"x3" triangle. We'll see what else it needs. I'm sure over 5.0" backspacing. My rear wheel lips are rolled allready.

Rear top of wheel lip = 26 1/8
Front top of wheel lip 25 1/2
Rear tires are 245/45ZR/18 (I have enough room to go about 2" wider)
Fronts are 215/40ZR/18 ( I need to go bigger, but they were a deal)

I am pretty sure my wheels are the #1

1) 18x8 Super Finish Black 5 on 4.5 +14 mm 4.989 p/n 3382-9828
2) 18x8 Super Finish Black 5 on 4.5 +2 mm 4.517 p/n 3382-9812