Finally got this achievement, based on solid advice on the Steam forums. I wanted to share that advice here as well, for what is one of the rarest CK2 achievements at the moment.
https://steamcommunity.com/app/203770/discussions/0/1678064284163976330/
https://steamcommunity.com/app/203770/discussions/0/1643164649205275442/?ctp=2
The short version of the above is:
a) start young;
b) have multiple traits that boost PCS;
c) join a warrior lodge;
d) be able to raid, so you can capture women and children to make lots of rivals;
e) get 80+ duel experience, and 20 duel kills.
A couple of additions to the above-
1. By educating children captured in raids, then choosing to make them ambitious when they complete their education, you can create many rivals. In 769 Africa, most rulers can't afford to ransom back their family members, so this was a good use for the dozens of children I had under house arrest.
2. Two starting rulers who make excellent duelist candidates are the Duke of Kanem in 769, and Harald Fairhair in 867. Both are 17, and have hardcoded traits that give them a high Personal Combat Skill. Fairhair has the better starting PCS, but Kanem has access to the African Warrior Lodge fetish artifacts, and was the one that earned me the achievement:


And here he is after 40 years of dueling glory. Not sure if I didn't get the duelist bloodline since I earned the Legendary Gathering bloodline first, or if it because I'm still playing on 3.1.0 (KKAD). Either way, he got the achievement, and was a lot of fun to play:

https://steamcommunity.com/app/203770/discussions/0/1678064284163976330/
https://steamcommunity.com/app/203770/discussions/0/1643164649205275442/?ctp=2
The short version of the above is:
a) start young;
b) have multiple traits that boost PCS;
c) join a warrior lodge;
d) be able to raid, so you can capture women and children to make lots of rivals;
e) get 80+ duel experience, and 20 duel kills.
A couple of additions to the above-
1. By educating children captured in raids, then choosing to make them ambitious when they complete their education, you can create many rivals. In 769 Africa, most rulers can't afford to ransom back their family members, so this was a good use for the dozens of children I had under house arrest.
2. Two starting rulers who make excellent duelist candidates are the Duke of Kanem in 769, and Harald Fairhair in 867. Both are 17, and have hardcoded traits that give them a high Personal Combat Skill. Fairhair has the better starting PCS, but Kanem has access to the African Warrior Lodge fetish artifacts, and was the one that earned me the achievement:
And here he is after 40 years of dueling glory. Not sure if I didn't get the duelist bloodline since I earned the Legendary Gathering bloodline first, or if it because I'm still playing on 3.1.0 (KKAD). Either way, he got the achievement, and was a lot of fun to play: