Hey @mokkin,
It seems like the switch node acts as if you would add a break; statement after each case in js, and thus only ever returns an output at the first match of your regex. You can see the same behavior with this simple test setup:
I think this is probably caused by line 688 here: https://github.com/n8n-io/n8n/blob/master/packages/nodes-base/nodes/Switch/V2/SwitchV2.node.ts
It would be cool if this option would be configurable and you could choose if the switch node is able to assign an item to multiple outputs.
I think your best option at the moment, is just to use 4 "IF-Nodes" (if you only have the four options you showed in your switch node config).
This way you would evaluate every option individually and bypass this problem.
I hope that helps 