It's all in the back spacing, it will fit no problem. I have 18x9.5 on the rear of my 67 with 265/40's, no lip roll are spring re-location. The back spacing that i am using is 5.75 but you can get away with 5.5.
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275 fits with NO issues. I had McCreary's 285/60/15 SH on my 68 which fit OK untill you went into a hard turn,or off camber bumps... then they rubbed. A 295 is 10mm wider (about a 1/4") and that just isn't going to happen w/o some work.
I was under the impression that a 5"+ b.s. was a no go (for some reason) ... I had no idea a 5.5"-5.75" would fit , I can get my fingers in between tires and inner fender with my 15x8.5" 5" b.s. convo pros (makes me nervous, haven't driven it, engine swap going on again)
btw I have mono leafs, how does the ride height compare (have multis on the f'bird)
Carl Casanova ran 275/40-17's on a 9.5" rim, 5.5" BS and rolled the lip.
69 RS Conv therapy program, Autogear M22, 8-pt cage, with a new 410! SOLD
New therapy program - 68 Coupe. Will be survivor exterior, modern underpinnings! SOLD
67 Belair with perfect floors, pinchwelds and firewall. Hmmm!
Yup, a 9.5 with a 5.5" and a 275/40/17 is the hot ticket. Unless your car sits severely off center, you shouldn't have to modify anything. Worse case scenario, you may have to roll your wheel lip on one side, or the other.
"The Custom Wheel Experts"