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I think the Rome 06 match, or the AO 05/TMC 05 final ones were all damaging to Federer. Had he won those. He would've never had any chokes or lapses in mental strength. Likely overcoming Djokovic on grass as well as a fair share of victories against Nadal on clay. He would likely have around 30 slams and 50 masters titles now.
 

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Losing to Hewitt in Davis Cup from two sets up steeled his resolve. He dominated Hewitt after that.
 
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