Oil leak out of top of filter bolt washer

It’s not uncommon for a copper washer, that’s been reused multiple times, to leak. Try the new copper washer as it came from the store. 10-15 pounds should be adequate. Make sure there are no burrs on the cap or the underside of the bolt head.
 
I can't comment on your specific question about which washers to try first but if you don't get a seal with the copper or plastic washers I suggest that you cut a washer from a piece of nitrile gasket material using the 7/16 steel washer as a pattern and put it on the bolt between a 7/16 steel washer and the filter top. Make the ID such that it's a snug, tight fit on the bolt. Moderate torque enough to stop the seepage and it should stop the leak. BTW, I purchased some stock hardware store 1/2 in and 7/16 steel flat washers last week and found the fitment to be the same as you described. In fact, the 7/16 washer was a snug fit on the 1/2 inch std thread bolt but would not fit on a 7/16 SAE fine thread bolt. If you need a hole punch try a large rifle spent casing on a block of soft wood. JMHO Stan
 
Make sure your filter cover bolt hole mating surface is clean & flat, so that the washer can seal. I have turned the cap upside down & carefully run it in circles on a sheet of fine Emory paper to make sure.

Also do the same to the underside of the filter bolt head.
 
I finally got this Cub oil filter cap to stop leaking by using the 7/16" copper washer I purchased from ACE Hardware for $2.33. Instead of the CASE/IH sourced one that leaked badly for $16! As noted earlier in this discussion, ACE Hardware evidently can't measure the holes in their washers very well. Every washer in the place marked as 7/16" actually has a hole that perfectly fits a 1/2" bolt. The washers from ACE are very flat and have no burrs or deformations on them from being punched out either. Like they were made just for this purpose. I also thank everyone for all of your suggestions as I cleaned everything carefully and polished the surfaces and checked for flatness. The whole problem was just a wrinkle in the original copper washer.
 
As noted earlier in this discussion, ACE Hardware evidently can't measure the holes in their washers very well. Every washer in the place marked as 7/16" actually has a hole that perfectly fits a 1/2" bolt.
FYI, they are made that way on purpose. It's called a clearance hole.
.4375 washer 1.JPG
.4375 washer 2.JPG
 
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I see. Thank you for this information. I came out of the structural steel and aircraft industry that wouldn't allow such sloppy clearances for their bolts and washers. I haven't checked any original washers on my Farmall, CASE/IH tractors to see what their clearances actually are. But I assume that higher grade bolts and washers have tighter clearances?
 
I went to NAPA for a copper washer on a hydraulic fitting. They didn’t have the size I needed. But could order it. The salesman told me to go to Harbor Freight and you could buy a hole box of various sizes for about the same as one of there’s. He was right I found one that worked perfectly and have more for future problems.
 
Same problem on my cub and SC and I used nylon or teflon (not sure what the material was) and that worked...I also spun the bell cover an inch at a time till everything worked and then marked it for next time. If it doesn't work, then I would get another cover.
 
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