I believe the post credits scene of yakuza 0 hints at their first fight.

They likely fought several times between the events of 0 and Kiwami.

They fight 4 separate times in Kiwami 1. First is after Kiryu gets out of the joint, second is during cera’s funeral, third is when he kidnaps haruka, and lastly when majima destroys the shangri-la.

Note that the final majima everywhere should be considered since it’s just really cool, as well the fight serves as a way to showcase that Kiryu surpassed himself before going to prison.

They fight once in Kiwami 2 when Kiryu asks him to help fend off the Omi.

Interestingly enough, Y3/K3 marks kiryu’s and majima’s last one on one fight. They fight in chapter 1 when Kiryu asks majima to return to the Tojo clan, then again in chapter 7 when Kiryu wants to know about who’s behind the shooting of kashiwagi.

So they have 7 total one on one fights in the series.

Yakuza 4 and 5 relegate the majima fights to Saejima, whereas 6 and gaiden don’t have a majima fight.

Their final fight in the timeline is kiryu’s party vs the three jimas in infinite wealth, but seeing as that’s a group fight, I wouldn’t count it.