Hi there, and welcome to the forum!
I have a calendar that I use for planning our month ends that is quite similar to this. My suggestion here would be that your "List of trainings" actually be built on a day by day basis, rather than date range. From there, you could pull this into summary tables (like you have with holidays on the front page) for "confirmed" or "soon to be..."
The next step would be to set up a conditional formatting rule set that checks the date vs each table (using Stop If True in the cf rule to control the order)