Of course that should work. You have 2 Options:
1. Use the TC2TR without RTP MIDI.
To do that, you need to configure the Box as Siimple UDP (see attached immage).
Then you can use the MIDI_TCP_Connector driver, but configure a UDP Channle with the IP Addres of the Kissbox (Port is 5007 by default as in the screenshot).
2. Use RTP MIDI Driver
In that case you have to configure the box as WinXP RTP MIDI and configure the Windows driver. Then you can use the MIDI TCP Connector and select the RTP MIDI Driver as output device.