CFF records do not matter in this milestone. It is just about 1A victories.
The only explanation I can give, and to answer your question (although this is not science but just a strong suspicion of mine) :
CFF makes a distinction between climb TT and flat TT.
You get this milestone after 5 climb TT wins
or 7 flat TT wins. (maybe logical, because there are many more flat TT races in an average season)
Leroy Benett ( SPORTLIFE ) = Buen Contrarrelojista, solo 2 
CC_Porco_Jones ( con Benny Andresen ) fue el primero y ya lo ganó el 13 de agosto.
Información : Obtendrás esta Distencione después de 5 victorias.
Probably you are wondering about Andresen now.
He is riding in the 2nd division so you cannot see his previous 1A victories (with the exception of the WC TT).
So your information is based on what he wrote in his notes. It seems to me he forgot to mention one victory in his notes, and just as Levin, Andresen got this milestone after 7 victories in 1A.
edit ; Another possibility is that there is a bug.
But if it is not a bug, this seems to me a logical explanation based on my suspicion about this subject.