Is that Old Timer stockman an 8OT? You're correct, it's 1095 steel on the older USA versions. These are great knives, and will sharpen up on almost anything. Knifenut is correct, in that diamond could be overkill, on this one anyway. If using diamond on 1095, going very, very gently with a fine diamond hone (like DMT's red/25 micron) will set a bevel very quickly on the Old Timer's blades. No need for anything more aggressive than that, with diamond. Even at that, the fine diamond will still remove metal from those small, thin blades very quickly. Much of the difficulty in using diamond on 1095 is, the diamond can create and erase a burr in almost no time. If one isn't really paying close attention for the burr formation, it might be missed when it happens. The natural inclination then, for most people, is to keep on grinding away at the steel. In a nutshell, it's easy to remove a ton of metal from a 1095 blade, and it seemingly never gets 'sharp' (as normally indicated by the burr formation).
Having said that, I have a '70s vintage Old Timer 8OT myself (as well as a 108OT, and a couple of 25OTs), and I just use some wet/dry sandpaper to set bevels (~400 grit) and/or maintain all of them (~1000+ grit, aside from stropping). I use a convexing method (edge-trailing, with the sandpaper on my leather-on-oak strop block). 1095 responds very nicely to this method. You can also use the sandpaper on glass, with an edge-leading stroke and light pressure, if you prefer a V-bevel.