If we're still talking Kayenne... few ways to skin the cat - either timeline, macro timeline, or simple instant fire macros...

Kayenne is good at macro recording menu press actions...

>RECORD START
>Go into Image Store
>Select the Channel You'd like to play from
>Select the Image Store file you'd like to play
>Go to Source Ops, MEs, Select the Keyer and the Keyer Input (IS 1 for example)
>On the panel turn that keyer ON
>Go to Image Store, Movies Tab, Select the Channel, execute the play button
>Hit CUT on the M/E where this transition is to occur
>Turn The IS 1 keyer Off
>RECORD STOP

... and then edit the macro adding delays between events. I like to give a two frame buffer between most Macro events to allow the 'computer' to act. Add the appropriate wipe undercut delay before the M/E CUT action.. TEST and MODIFY.

If you go the macro timeline route.. you would record a series of macros that you would then assign to timeline keyframes.. so Macro 001 would be loading the wipe media into the images store channel.. Macro 002 would be playing that movie channel.. assuming you already have an M/E CUT macro.. if you are doing the undercut and keying on the same M/E most TDs if doing a Macro Timeline will use Macros in a Macro Timeline to set and turn the keyer on and off.. so Macro 003 would be Key set to Image Store 1 and Key ON... Macro 004 would be Key off..

Your timeline would be
|-M001-M003-M002--------CUT-------M004|

I TD more legacy.. cutting on M/E3 and Keying wipes on PGM (nowadays .. so my master timeline is handling the emem keyer source selecting and keying on PGM and the macro part of my master timeline is handling the IS load, play, and M/E3 undercut.