Conditional formating (with range) but instead of the color/formating of the certain cell to get values inside the matching cells in the range?

[aircarrier]

Hello everyone,
this is my first time here, didn't know such a great community exists. Usually I was struggling on my own in MS Excel.

I need the help since I need to figure out how to place certain values (which will be manually written in table section with 5 headers) in the appropriate calendar range e.g for 2 year (24 months) template that's prepared starting from the date when the contract is made.
We will have 5 checkups and date when they will happen and who will be executing or what percentage is needed (not yet clear but somehing of those two).
So each of 5 checkup needs to be placed inside the matching month in "calendar" and place the value that is inside that checkup month descripion counting the date when contract is placed.

I honestly don't know how to do it.

I have already prepared Conditional formatting (with range and that matches months) with coloring and got idea if the same is possible but instead of the color/formating of the certain cell to get values inside the matching cells in the range? This would solve it but I guess that it's not possible.

Thanks to everyone in advance that helps with this

 

[aircarrier]

Left part in the image is how it should look like after it is populated from the data from the right.