Note: you have done > in both cases above, should they be different? It doesnt matter though, because you cant do conditional branching in roll20 macros. There's no way to modify a roll based on that roll's value without using the API (a Pro subscriber perk). If your GM has Pro, a script could be written to do the above, but it's not as easy as creating a macro. For really simple conditionals, you can sometimes fake it with roll20s keephighest and other functions, but this isnt one of those cases.