Once upon a time there was a developer trying to play IT and install trac on a windows 2k3 server.
He used the guide located at http://trac.edgewall.org/wiki/0.10/TracOnWindows#Method2:UsingInstallers
From this guide he learned about using various software with different versions (installed in this order):

svn-1.4.6-setup.exe
python-2.4.4.msi
clearsilver-0.9.14.win32-py2.4.exe
pysqlite-2.3.4.win32-py2.4.exe
svn-python-1.4.4.win32-py2.4.exe
trac-0.10.4.win32.exe