Does Cubase Elements 9.5 have an “annotation track”, in which you can enter random text (like Roman numerals for the chords) as an event?
Bumping because I’ve never seen one but maybe someone else has.
Regards 
You can use the Marker Track for that I guess, but there’s no dedicated track type for random text in any version.
The Score Editor in Cubase Pro allows you to add random text or chord symbols using the menu to the left, but I don’t know if this is also possible in Cubase Elements.
You can also add text to notes in the Key Editor. The Info Line must be made visible by clicking a button near a cog icon to the top right.
There has been feature requests regarding a lyrics track with TelePrompter integration.
Something like that could also be used for other data.