With both of those players abstaining from the US Open due to the risk posed by COVID-19, this year's tournament looked like a promising opportunity for the Serbian to inch even closer to meeting them at the top of the grand-slam-wins list. (With 17 titles to his name, he's just two behind Rafa and three behind Federer.)
Then came his disqualification.
Djokovic was defaulted during Monday's fourth-round match after he blindly hit a ball in frustration that struck a line umpire in the throat.
The world number 1's loyal fanbase are livid at his forced exit, and a particularly vengeful minority have left abusive messages on the umpire's Instagram account, one of which even celebrated the 2008 death of her son.
But Djokovic's many, many critics claim his decision to sulk out of Flushing Meadows without speaking to the media is yet another stroke in a pattern of entitled behaviour.
Indeed, it's hard to imagine that the commentary would be quite so thick with Schadenfreude had any other top-five player swung that tournament-ending racket.