I have NHL '95 running on my Windows 10 PC by using dosbox, and Toni Whilen's NHLINFO editor works as well.
Hrm, I haven't tried dosbox on my new Windows 10 computer yet. I might have to look that up (you may have opened up Pandora's Box for me).
Downloaded '95 and successfully started it up. That opening music still makes me smile. Grabbed the editor but didn't have the time (aka didn't want to tempt myself to stay up to 2am maniacally updating rosters) to try it yet. But my memory did get jogged and I think I tried it back in the day and didn't like the interface. I have a different editor which still works on a super old laptop that takes like 20 minutes to boot up.