Only if Winamp is set as the default playlist player first

Prefs (Ctrl+P) -> Filetypes : select PLS & M3U (and any others of your choice)
Only problem with playlists is that:
1) it will always play the first track in the list
2) it will overwrite whatever was previously in the playlist
3) you end up creating loads of saved .m3u playlists to cater for all your needs/moods, and also could end up creating loads of relevant shortcuts to match. Hey, I once had a whole folder dedicated solely for this purpose, lol.
Of course, some people don't mind, whereas others do.
Best bet in the end is to use the Run command, or one of the alarm plugins . . . unless you only have one saved playlist and don't mind it always playing track 1 first (though the way round this would be to leave Winamp in shuffle mode).
Heyhey, the possibilities are almost endless.
note to self:
Seems no matter where I go, there's no escaping Winamp for me
