Bit of a late reply but I started playing this game last night and was having similar issues with a number of achievements (practically all of them actually).
Cranking the difficulty up to Legend certainly helps (adjust the sliders to make your life easier)
Also, with the Rope-a-dope achievement I had to spring off the ropes at least 15-20 times before it finally noticed I had met the criteria, lol. I haven't tried the Paycheck achievement yet but I would imagine it's a similar principle.
Not incredibly helpful advice obviously but I'd basically knock the difficulty up to max and just keep meeting the criteria until they pop (at least they pop mid-match!)