Ok people, I think I have figured It out. I have decoded the 101 Dalmatians timeline:
Ok, so Cruella is the OoT of this timeline. From that movie comes the three variations of the similar events. And these three timelines consist of:
-The Classic Timeline: this timeline takes place 10 years after the events of Cruella where the character aged really fast and became insane with age, losing all ownership of her mother's company. The original 101 Dalmatians kicks in this timeline, which is quickly followed by 101 Dalmatians 2 and then years after the timeline continues in the future with 101 Dalmatians Street.
-The Glenn Close timeline: this is an alternate reality where Cruella took longer to fall into deep insanity and managed to take full control of her mother's company. Somehow Roger dropped out of music as he found a better career in videogames and Anita decided to go work for Cruella after all the events which transpired. This timeline is made up by 101 Dalmatians and 102 Dalmatians.
-The USA timeline: this timeline features a weird variation of the events from the classic timeline, where at some point the main Cast from Cruella decided to move from London to the USA and Cruella never got the restraining order during the seemingly events from the classic movie. This timeline is made up only by the early 2000s cartoon and maybe the alternate version of 101 Dalmatians which may have took place in the USA on this timeline.