Hello ,
Looking forward to find the best way of rolling an object around cylinder smoothly, as given GIF sample . Please assist what I should follow in Blender? I’ve tried cloth modifier but not successfull… 
Add Modifier > Simple Deform should do the trick. Search up for tutorials if you dont know how to operate it. There’s many…
thanks for your reply. I’ve given a check with simple deform modifier- settings and tutorials briefly, but it does not exactly help to roll the mesh(tried all settings, subdivied as well) around cylinder. any further method would be suggested?
For anyone who’s stuck at this point, the problem is figured out via “Simple Deform” modifier.
The trick is that; you have to add an “Empty arrow”, let modifier work in conform with the empty arrow so that the required shape-simulation can easily be created.