kks,
Sorry, I was writing my second reply while you posted your second post.
Can you post a photo of your filter and where it is plumbed into the block?
There were several brands and styles of canister oil filters. They filled and drained in different ways. The outflow of the filter should go to the hole closer to the front of the block.
Here is a photo of the locations of the holes on a 1954 block. Even if your oil filter was/is blocked, I think it should not leak.
