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I think I can take a look for you on Wednesday. My 58 currently has a 59 grill and I have 58 headlight trim laying around. I have the 58 headlamp assemblies in it now, don't remember exactly how but I think they fit with a couple of well placed drilled holes. I'll pull out the trim and see if there is a way to install it. The 60 (and, of course, the 57) grills are totally different but the 58/59 are very similar. I'll get a look at it as soon as I can and get back to you here.
I was finally able to get into the barn to take a look at my truck. It is exactly as I described (59 grille with 58 headlight buckets) which is what, I think, you are looking for. The method of attachment is completely different from 58 to 59. The 1959 headlight trim attaches with 2 clips on the grille at the top and a screw into the grille at the bottom. The 1958 headlight bezel attaches directly to the headlight bucket itself. When I put the 1958 trim on the truck, it matched up to the headlight assembly perfectly but it stood "proud" of the grille in some places by as much as a 1/2". So the answer is "Sorta." While it does fit and will bolt up, it does not match up with the grille at all. If you are going to leave the 59 grille on your truck, you will need the 1959 headlight buckets and headlight doors too. My truck has been running around with a 59 grille waiting for a salvageable set of 1958 headlight doors for years. Now that I have them, it won't be long before I install my N.O.S. 1958 chrome grille and get that part of the truck back to original.