Always On Top Program Won't Stay On Top

[fatman]

In my specific instance, I am trying to have livesplit with a game that I am playing on windowed borderless. I have set it up so livesplit is Always On Top. I would expect that a borderless windowed mode game would apply to that, as it is technically a window. However, when I click on the game, livesplit goes below it. Can anyone tell me if I'm doing something wrong or it's just gonna happen?

[Friendly Madness]

Bump, I'm also having this issue, I have my twitch chat to stay ontop of everything accept my game (which is also in windowless bordered mod.)