I can’t see how to do it… am I being dumb? I don’t have a “Match” button like on this article: https://support.trainerroad.com/hc/en-us/articles/360016262412-Match-a-Planned-Workout-with-a-Completed-Workout-Ride
I take it you have created the workout first?
A ride completed after doing that should automatically associate with it. Or you can do the match thing.
Im pretty certain you need to have the outside ride completed first and uploaded on the same calendar day (or dragged to the same calendar day) for the ‘match’ option to show up.
If you still dont see it appear, feel free to check in with email@example.com and they can take a look.