How would I feel if I lost to a player 7 times in a row? The same way Djokovic felt when he lost to Nadal 5 times in a row. 5, 7, it makes no difference.
I think it would make a difference as to when the defeats occurred. Exhibitions? Not a big deal. Davis Cup? That's manageable. Quarter Finals? That's not too bad. Finals of majors and the surfaces where you're considered the king? That's gotta mean more.