Dyna Glide ModelsSuper Glide, Super Glide Sport, Super Glide Custom, Dyna Glide Convertible, Super Glide T-Sport, Dyna Glide Police, Dyna Switchback, Low Rider, Street Bob, Fat Bob and Wide Glide.
Never had one or any trouble with it for that matter. Does your cover had slots or holes in the front? If not then I don't see where you'll have a problem.
If that takes a standard round K&N, you can get the HD sock for 25 bucks. If it's a flat style, you really don't need it as the cover should provide all the protection you really need.
I switched to the plain tear drop to the model with the slots (Desperado?) a few years ago and no issues with rain on that model either. The teardrop is a proven cover for a lot of years. You should be fine.
I run an open round well oiled KN filter never had a problem with rain and I have ridden through some really heavy down pours. If you have any cover on it now you will be fine.