Sending MIDI via Tip *and* Ring on the MC3?

Is it possible to set the dip switches on TRS ports 3 and 4 to send MIDI to the ring and the sleeve at the same time? I mean, I know the switches can be set like that, but will it actually work? One use-case would be splitting the TRS cable to send MIDI to a Chase Bliss Audio pedal as well as and Alexander Effects pedal.

Thanks!

[edited for the TS/TRS confusion]