What I would do is the following steps:

1. use IDA Pro to get all functions names and addresses (hopefully names if you renamed any of them) in the binary and export it as a python dictionary. examples can be found here.
2. Install PyKd as described here.
3. Create a PyKd script to set conditional breakpoints to print something everytime they are hit and then continue execution, like:

import pykd
funcList = { 'funcA': 0xAAAAAAAA,
             'funcB': 0xBBBBBBBB, 
               ...
           }

for funcName, funcAddr in funcList.items():
   pykd.DbgCommand('bp ' + funcAddr + ' ".echo ' + funcName + ' executed; gc"')

4. Execute in WinDbg:

.load pykd
!py <path to script>
g

this will trace each function during the execution with the function names from your IDA Pro database.

What I would do is the following steps:

1. use IDA Pro to get all functions names and addresses (hopefully names if you renamed any of them) in the binary and export it as a python dictionary. examples can be found here.
2. Install PyKd as described here and here.
3. Create a PyKd script to set conditional breakpoints to print something everytime they are hit and then continue execution, like:

import pykd
funcList = { 'funcA': 0xAAAAAAAA,
             'funcB': 0xBBBBBBBB, 
               ...
           }

for funcName, funcAddr in funcList.items():
   pykd.DbgCommand('bp ' + funcAddr + ' ".echo ' + funcName + ' executed; gc"')

4. Execute in WinDbg:

.load pykd
!py <path to script>
g

this will trace each function during the execution with the function names from your IDA Pro database.

What I would do is the following steps:

1. use IDA Pro to get all functions names and addresses (hopefully names if you renamed any of them) in the binary and export it as a python dictionary. examples can be found here.
2. Install PyKd as described here.
3. Create a PyKD script to set conditional breakpoints to print something everytime they are hit and then continue execution, like:

import pykd
funcList = { 'funcA': 0xAAAAAAAA,
             'funcB': 0xBBBBBBBB, 
               ...
           }

for funcName, funcAddr in funcList.items():
   pykd.DbgCommand('bp ' + funcAddr + ' ".echo ' + funcName + ' executed; gc"')

then execute in WinDbg:

.load pykd
!py <path to script>
g

this will trace each function during the execution with the function names from your IDA Pro database.

What I would do is the following steps:

1. use IDA Pro to get all functions names and addresses (hopefully names if you renamed any of them) in the binary and export it as a python dictionary. examples can be found here.
2. Install PyKd as described here.
3. Create a PyKd script to set conditional breakpoints to print something everytime they are hit and then continue execution, like:

import pykd
funcList = { 'funcA': 0xAAAAAAAA,
             'funcB': 0xBBBBBBBB, 
               ...
           }

for funcName, funcAddr in funcList.items():
   pykd.DbgCommand('bp ' + funcAddr + ' ".echo ' + funcName + ' executed; gc"')

4. Execute in WinDbg:

.load pykd
!py <path to script>
g

this will trace each function during the execution with the function names from your IDA Pro database.