Hi Whitesell. Welcome to the forum.
If you are not aware of it already the lookup functions find only the first instance of lookup_value it finds in table_array. To return multiple instances you will need an array formula (or maybe helper columns).
If you aren’t familiar with array-entered formulas array enter means the formula must be committed from edit mode by simultaneously pressing and holding down Ctrl and Shift while hitting Enter.
Try array entering this formula in B13 of 'Calendar (2) and fill down to B17. Then fill across to column H. You will have to repeat for each week. Note the absolute row reference for day. It permits copying one formula all referencing the same row#.
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