What are you trying to accomplish for a cross-fade?
Try the following settings in the DirectSound Output fading tab...
- Winamp > Ctrl+P (for Preferences)
- Plug-ins > Output
- Nullsoft DirectSound > Configure button
- Fade tab
.. -- Highlight 'on start' > check-mark 'Enable' and 'Use custom fade time' > set fade time of 4000 ms
.. -- Highlight 'on end of song' > check-mark 'Enable' and 'Use custom fade time' > set fade time of 3000 ms
- Apply button > OK button > if asked to automatically increase buffer length, click Yes
- close out of Prefs