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I feel like Diavolo would easily get overwhelmed, prep or not. Ghiaccio and Risotto alone would already be problem enough since he can't heal himself like Giorno and would be ****** once one of his limbs is frozen.
Diavolo has the benefit of being familiar with the stand abilities of all the members of La Squadra (Barring Risotto, although if this post-Metallica Diavolo he would); meaning he likely doughnuts Illuso or Prosciutto after immediately activating King Crimson.
The rest of La Squadra fall in short order due to Epitath and time erase, barring Ghiaccio and maybe Risotto, the former of which has a stand which honestly has the best chance of forcing Diavolo to keep his distance. Especially since Diavolo isn't aware of its weakpoint.