Version:            (using KDE 4.3.4)
OS:                Linux
Installed from:    openSUSE RPMs

Window-specific options are not applied automatically, if window title match is used (in any form - exact match, substring match or regexp). However, these options could still be applied by clicking window menu -> advanced -> special window settings -> OK.

How to reproduce (using kwrite for example):
1. Create a couple of files - 'first.txt' and 'second.txt'.
2. Open 'first.txt', create some specific options for it (I've used position, size and shortcut) using window title match (Substring search: first).
3. Open 'second.txt', create some specific options for it using window title match (Substring search: second).
4. Close both files. Open them again. Window-specific options are not applied.
5. Click window menu for one of the files, select Advanced -> Special window settings. Window settings are identified correctly - all values are these set for this particular file.
6. Click 'OK'. All window-specific options are applied to both of kwrite windows.