GRID 2
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You rOCDed!
By Cpt. Coño
For a lot of players this achievement doesn't pop, even after finishing the entire campaign with all races and events marked with either a 1st position badge or a checkmark. This guide will tell you which events to focus on, so you (probably) don't have to replay the entire campaign.
   
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What's up with this achievement?
The achievement description is "You finished first in every career event, during season play and/or via the timeline."

This is 100% the truth: you have to actually win all events (not races, but events). The issue is that especially Endurance events will be marked as completed (green checkmark) without you actually having to win them. Sometimes it's enough to end in third place for example, sometimes you'll have to beat a particular opponent.
What events to focus on
These events are probably the culprit for you not getting your achievement. Making sure you finish in first place on these events via the timeline will hopefully save you from replaying the entire campaign. To make it easier for yourself, I'd advise to turn the difficulty down and set damage to visual damage only.

WSR 5: ESPN Endurance

WSR 1: Motor Mavens Endurance

Season 2 (clubs): Emaar Endurance

WSR 3: Rockstar Energy Endurance