By "crossfading" do you mean simply fading out when stopping, or skipping to a new track, and the new track fading in when resuming from pause, or beginning from a skip from another track? If so, Winamp 2.80 has this feature. I think you may have to specify this output device manually in the plugins or something, if you'd manually selected something different than the default before (it's named something with the word "fade" in the title). I didn't really like it when it came out (2.7x or 2.80), but now I think it's pretty nice.
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