Is Overeem-Werdum 1-3 the longest spanning trilogy in MMA history?

Only trilogy that is close to that is Vitor/Hendo.

Royce vs Ken i guess, but that fight never should have been made.
 
Royce vs Ken

This was easy...

https://en.wikipedia.org/wiki/Royce_Gracie

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I wonder if technically those 3 fights were in different sports: 1st is Vale Tudo, 2nd is NHB, 3rd is MMA.
 
Chuck Tito gonna take it by years end.
 
Chuck Tito gonna take it by years end.
I don't think so.

Royce Gracie and Ken Shamrock fought on:
November 12, 1993 (UFC 1)
April 7, 1995 (UFC 5)
February 19, 2016 (Bellator 149)

That's 22 years, 3 months and 7 days.
 
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