Yakuza Kiwami

These 4 achievements are some of the more annoying ones because they rely on randomly running into the correct guys. If the Mad Dog fights are not spawning for you then you are not far enough in Majima everywhere. You must have done the trigger event at rank S to make the Mad Dog fights happen. At specific locations there are people who are alone and looking for a fight, they will look like yakuza but only one at a time. The guy will not always be there are you may have to go in and out of the local buildings to try and spawn him. you will know when you encounter him because a dialogue box will start and the guy will verbally challenge you instead of initiate a fight to begin.

For Mad Dog of Shimano to appear you must either go to the Mach Bowl enterence, or outside the Millennium Tower a man in a black jacket and sunglasses will be seen, just go in and out of Taihei Akaushimaru to get him to spawn.