Thing was a lot of Microsoft APIs for GUIs and whatnot used the List and if you wanted to use the List<X> you had to copy the list or make a wrapper or something. You might say, "just use the List" but at that point (circa 2008) I had to also use the List<X> for some API so I always had to do some conversion.
Then, when WinForms or WPF wanted a list, you could just give it a List<T> instance, and it would talk to it via IList, boxing and unboxing if necessary.
What you describe happened in the other direction - if you had, say, a generic method operating on IEnumerable<T> or IList<T>, and wanted to pass it a WinForms collection. WinForms generally defined strongly typed collection classes on a case by case basis, but none of them implemented the new interfaces. It was there where you had to wrap things, most often using AsEnumerable<T>().
I was at a conference on scientific programming in Java very early on that Geoff Fox put on up at Syracuse and we had a list of requests from Sun that they didn't give us but Microsoft gave many of them right away.
On the other hand I really like Java's all-virtual approach to inheritance because the .NET model gives programmers more ways to screw up and get confused.
Both languages slipped in generics after 1.0. Java used type erasure in a way that made it so a List<String> is really a List so generics could be retrofitted easily to existing code. .NET's implementation of generics let you do more but caused a rift in the ecosystem between generic and non-generic collections.
I'd say long term Oracle's stewardship of Java has been very good. JDK 8 puts lambdas on your fingertips with a very fluent syntax that belies the idea that Java is terribly verbose. Since then Java has gotten steadily better release after release while maintaining great compatibility.
I work with people who are conservative about updates because they are worried about breaking things but for the last few LTS releases I've said "it ought to be really easy, let's give it a try" and it is really easy and we get performance improvements we can feel.