Completed Hitman Legacy Sapienza and played The Icon before getting to level 20, then after getting to level 20 (a round 54% challenge completion) it didnt pop. I have since restarted my ps4 pro numerous times, completed more challenges, completing the level and watching the score total up to completion many times (I am at 77.8% mastery now.
It’s a known trophy bug. Details have already been given to developers and they are aware of the issue. They are currently working on a fix as mentioned in the patch notes. Not to worry, it will be fixed