If the expense_year column contains date values but only displays the year then they aren't going to match the year in the annual_expense_year cell.

There are probably a few ways to handle it, for example use criteria to find dates in the expense year that are between the start and end of the year in annual_expense_year.

Can you upload an example workbook?

Click on GO ADVANCED and use the paperclip icon to open the upload window.