2008 for sure. Federer was in prime and hitting far better than this, Nadal was in prime. You can tell he won't lose no.1 easily if he had fire, no fire contributed to early losses in those Masters.
Umm, he was past his prime and struggling with mono. He had a worst clay court season than this year and was bad at the FO pretty much throughout.
To be fair I actually thought he played better in the final, but was just shut out by a superior clay courter at his best.
There were similar conditions actually, and Fed has never dealt with slow dirt particularly well.
This loss was worse in the sense that Novak played poorly as well.