Here is using the formula:
=IFERROR(TRANSPOSE(INDEX(Sheet2!$B$1:$B$5,SMALL(IF(Sheet2!$A$1:$A$5=$A2,ROW(Sheet2!$A$1:$A$5)),COLUMN(A$1)))),"")
Above is an Array Formula entered using Ctrl+Shft+Enter in Cell C2 and copied to the remaining cells of interest.
Assuming your data is organized like below:
Sheet1:

Outstanding sheet:

Here is the code:
Sub test()
Dim ws1 As Worksheet, ws2 As Worksheet
Dim myfilters
Dim myfilter
Dim rng1 As Range, rng2 As Range
Set ws1 = Sheet3
Set ws2 = Sheet2
Application.ScreenUpdating = False
With ws1
Set rng1 = .Range(.Range("A1"), .Range("A" & .Rows.Count).End(xlUp))
myfilters = rng1.Offset(1, 0).Resize(rng1.Rows.Count - 1)
End With
With ws2
.AutoFilterMode = False
Set rng2 = .Range(.Range("A1"), .Range("A" & .Rows.Count).End(xlUp))
For Each myfilter In myfilters
rng2.AutoFilter Field:=1, Criteria1:=myfilter
rng2.Offset(1, 1).SpecialCells(xlCellTypeVisible).Copy
rng1.Find(myfilter, rng1(1)).Offset(0, 2).PasteSpecial xlPasteValuesAndNumberFormats, , , True
.AutoFilterMode = False
Next
End With
Application.CutCopyMode = False
Application.ScreenUpdating = True
End Sub
Not tested though.
So test it in a duplicate data for safety.
Hope this helps.