This answer is dependent on the data being arranged sequentially by date as in the sample file. F4 contains the array formula (Ctrl + Shift + Enter)
which dragged across also populates G4:H4. I4 contains the array formula
which gives the row number of the next date, expense type and cost. F5 contains the formula
which can be copied across to column H and then down as far as needed. You will need to change the formatting in column H back to currency afterwards. Here is your file with these formulas included, note that I put a simple data validation drop down in F3, which could be easily improved by creating, and hiding, a pivot table of dates from column A.
Copy of Index - Match Question.xlsx
Let me know if you have any questions.
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