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I do believe restarting the story wipes all of your challenges. You need to see 160/160 to have the achievement pop. If you encounter a challenge that the game absolutely refuses to grant (there are several mentioned in this guide) then feel free to use the Giant Accomplishment Save File linked in the Introduction section.
As a sidenote, replaying the mission should update your score in Career Mode, as long as the new score is greater than the old score. It does not matter whether you Rewind the Story or simply replay the mission.