The crossfader not working via the Bento/Modern EQ is a known bug in 5.9.0 which will be fixed for 5.9.1 - coming soon.
For now, you can manually edit the "Fade on end of song" value via:
Winamp => Prefs (Ctrl+P) => Plugins => Output => DirectSound Output (out_ds.dll) => Config => Fading tab.
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Crosfade not working
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