Hi Hellplay,
I have been playing with this idea and have come up with this. if you follow this guide you will have it all done but you don't need to use the wording have as that was for testing only.
This shows it working for a win and lose.

To get this all work first make the cmd you want to start this whole thing off mine was !die

This is the cmd= Ok @user@ and @target@[1] Have gone into battle
now make sure you add the command chaing part= !die2 @user@ @target@[1]
and tick the box Admin access and the run after is for your liking. now we go onto making the next cmd.
all the cmds name what you want as you will see i used die1 to die5 so you see how it all links.

!die2 = @if@[>||@rand@[0,100]||50||!die3 @target@[1] @target@[2]||!Die4 @target@[1] @target@[2]]
with this Cmd this part will make it 50/50 on who wins"[0,100]||50||".no chaining required for this one but do make sure hide from cmd list is ticked on all the next cmds.

!die3= Ok @target@[1] Won the battle And @target@[2] Lost
Cmd Chaining= !add 200 @user@

!die4= Ok @target@[1] Lost the battle And @target@[2] Won!
Cmd Chaining= !die5 @target@[1] @target@[2]

!die5= !remove 200 @target@[1]
Cmd Chaining= !add 200 @target@[2]
for all the cmds just name them for what you want and change them in all the cmds.
Regards,
Ian Chandler