Multiple Criteria Index/Match Function in VBA Looking Up Dates/Strings/Numbers

I cannot seem to get this to work and i am hoping one of the resident experts can shed some light on what i am doing wrong.

Essentially, I am trying to use a combination of Index and Match functions from within VBA to identify multiple criteria and then return a related value from another column in the identified row. I have attached a sample file with the following 2 simple scenarios:

On a Userform are 2 scenarios:

Single Criteria [WORKING] - Selecting a date from the top combobox triggers the macro to match the selection with a column on the "Raw Data" sheet. It if there is a match it puts the corresponding value from column C ("Flag") into the top label on the userform.

Multiple Criteria [NOT WORKING] - Selecting a date from the bottom combobox triggers the macro to match the selection with a column on the "Raw Data" sheet. It also attempts to match a string (stock symbol) from the "Main" worksheet in A2 to a column on the "Raw Data" worksheet. The bottom label on the userform should only show a value if both criteria are met.

After spending some time on this and learning about the behavior of the Match function in VBA i think i have gotten very close... but i am still missing something. Hopefully it is syntax related. Any help would be greatly appreciated!

Single Criteria Code[Working]:

Private Sub combobox1_Change()
    Dim TheDate As Date
    Dim TheSymbol
    Dim Match As Variant
    Dim colSymbol As Range
    Dim colDate As Range
    Dim colFlag As Range
    
    TheSymbol = Sheets("Main").Range("A2").Value
    TheDate = Menu2.combobox1.Value
    
    With Worksheets("Raw Data")
        Set colSymbol = .Range("A2:A" & .Range("A65536").End(xlUp).row)
        Set colDate = .Range("B2:B" & .Range("B65536").End(xlUp).row)
        Set colFlag = .Range("C2:C" & .Range("C65536").End(xlUp).row)
    End With

    On Error Resume Next
    'ONLY 1 CRITERIA & 1 CRITERIA RANGE
    Match = Application.Match(CLng(TheDate), colDate, 0)
    On Error GoTo 0

    If IsError(Match) Then
        msgbox "Not Found"
    Else
        Menu2.flag01.Caption = Format(Application.Index(colFlag, Match, 0), "X")
    End If
End Sub

Multiple Criteria Code [Not Working]:

Private Sub ComboBox2_Change()
    Dim TheDate As Date
    Dim TheSymbol
    Dim Match As Variant
    Dim colSymbol As Range
    Dim colDate As Range
    Dim colFlag As Range
    
    TheSymbol = Sheets("Main").Range("A2").Value
    TheDate = Menu2.ComboBox2.Value
    
    With Worksheets("Raw Data")
        Set colSymbol = .Range("A2:A" & .Range("A65536").End(xlUp).row)
        Set colDate = .Range("B2:B" & .Range("B65536").End(xlUp).row)
        Set colFlag = .Range("C2:C" & .Range("C65536").End(xlUp).row)
    End With

    On Error Resume Next
    'MULTIPLE CRITERIA & MULTIPLE CRITERIA RANGES
    Match = Application.Match(CLng(TheDate) & CStr(TheSymbol), colDate & colSymbol, 0)
    On Error GoTo 0

    If IsError(Match) Then
        msgbox "Not Found"
    Else
        Menu2.flag01.Caption = Format(Application.Index(colFlag, Match, 0), "X")
    End If
End Sub