See number of steps into debugger

Is there any way to see how many steps or processes into a debugger you are? For example, if I have a bug and it's only occurring on the tenth iteration through a process, is there counter that keeps track of how far into the process I am? The intended use is that I watch this number and keep clicking through the debugger until the program fails. Then the next time I go through the debugger I can quickly move ahead up to this point. It doesn't really matter what the process is tracking (operations, number of function calls, etc.) as long as it steadily increases. Also, if this does exist, is there a way to jump right to a specific point?