2008 Skate Canada: Chan was overall the best between SP and FS (3rd and 2nd), and lost both segments, but Ponsero (who led after the SP) crumbled in the FS, and Bradley (who won silver) had a mistake in the SP and wasn't nearly the level of Patrick's artistry in general.
2008 TEB: Certainly deserved the win. Clean SP, where Kozuka missed an entire spin. Made some errors in the LP, but Kozuka fell on a UR'ed quad -- essentially the SP made the difference.
2010 Skate Canada: arguably should have lost to Oda (considering the SP), however, Oda fell in his FS and had other errors (and was probably underscored on PCS). Home ice certainly helped with the win, but he had a pretty decent FS.
2011 Japan Open: Bad competition overall, but even with 3 falls, Chan arguably deserved the win if you look at the scores and errors of his competitors. Gachinski (who had a fall) had almost the same technical level due to much weaker non-jump elements, and of course, Chan easily beat Gachinski on PCS. Kozuka/Takahashi URed jumps and fell on his quad. Buttle doubled many jumps.
2011 Skate Canada: Chan fell twice (neglected to do a 3rd combo, but not a visual error) and Fernandez fell once and doubled a 3L. Better GOE for Chan essentially gave them the same TES mark, and of course Chan's PCS was better. Chan deserved to win the FS over Fernandez by a margin that made up for Fernandez's lead in the SP. This, however, is an example of a victory where a relative new star on the scene - much like Ten at 2013 Worlds, Javier was disadvantaged by not having any previous success - Skate Canada was however the start of a breakthrough season for him technically and artistically -- had Fernandez had his 11/12 season already under his belt, he probably would have beaten Chan at this particular competition.
2011 GPF: Takahashi had a poor SP; in the FS Chan made more errors (and probably deserved to lose the LP), but his BV was still higher than Takahashi by about 5 points which made up for the errors. Maybe he didn't deserve to win by 11 points but certainly a considerable margin.
2012 Worlds: Again, Takahashi had errors in the SP (the downgrade was essentially the same cost of Chan's 2A fall) that opened a margin between Chan and him. And in the FS, Chan's 2 quads garnered enough points to make up for the 2A fall. They both had similar BV, even if Dai visibly skated cleaner.