Kim - Lyman was/is a company that originally made reloading equipment and a few other sporting products, and its my understanding that they made some reloading equipment for the gun makers who stamped them with their brand sometimes. When the Model 1994 Winchester came out it was in .32-40, .38-55, then in 1900 came out with the famous .30-30 and there are two other calibers which I can't bring to mind at this time but will look it up if you like. These old rifles bring lots of bucks and the accouterments do also if they are stamped with the gun manufacturer's name.
More than likely your grandfather bought the tools at the time he bought the rifle. I have one Lyman mould and handles that I use a lot.
It is identical to the one you show in the pics. I'm not familiar at all with the loading tool, it doesn't look at all like the Lyman tool I have.