Keep in mind the '69 Cutlass came with 14" wheels. Putting wheels almost TWICE as big as the originals is just a bad idea. Even though you probably CAN cram them under there, you will most likely have clearance problems. The car will sit as high as a pickup truck but drive and handle worse than a pickup truck.
No it will not fit correctly with the grill.
Not likely why not just use the correct part?
it will fit but you will need to drill out an ignition switch hole unless you also transfer over the 69 steering column.
Yes but the hood latch has to be relocated.
I have a 1969 Oldsmobile Cutlass supreme. My car has a 1968 front bumper, hood, and grill. Its mirror of your question but If a 68 can go on a 69 I wouldn't see why a 69 couldn't go on a 68.
yes i have 26s on mine.shave wells -lift kit
Yes
No
how do you fit 26 inch rims on a 1988 chevy caprice classsic
please make them fit
No, they're 2 totally different bodystyles.
Yes you can fit 20" rims on you 1979 cutlass, if you wanted to you could fit 22" rims with low profile tires with the stock springs.