Hello petsean007. Welcome to the forum.

There is a typo in Sheet1 A8 ... a missing space. Once corrected try this in O2:U3 of Sheet1.
Formula: copy to clipboard
=IFERROR(INDEX('Sheet 2'!$F$2:$F$100,AGGREGATE(15,6,(ROW($A$2:$A$100)-MIN(ROW($A$2:$A$100))+1)/
((O$1='Sheet 2'!$A$2:$A$100)*($A2='Sheet 2'!$D$2:$D$100)),1)),"")