Public Class frmDGVDateIcon
 
    Dim bs As New BindingSource
    Dim WithEvents dgv As New DataGridView With
        {.Parent = Me, .Size = New Drawing.Size(300, 300), .DataSource = bs}
    Dim dt As New DataTable
 
    Dim dateok, nodate As Bitmap
 
 
    Private Sub frmDGVDateIcon_Load(sender As Object, 
                       e As EventArgs) Handles MyBase.Load
 
        'Einige Demo-Daten
        dt.Columns.Add("Date", GetType(DateTime))
        dt.Columns.Add("Icon", GetType(Bitmap))
 
        With dt.Rows
            .Add(Nothing, Nothing)
            .Add(New DateTime(2020, 12, 10), Nothing)
            .Add(New DateTime(2020, 12, 13), Nothing)
            .Add(Nothing, Nothing)
            .Add(New DateTime(2020, 12, 16), Nothing)
        End With
 
        'Datenbindung herstellen
        bs.DataSource = dt
        dgv.Columns("Icon").MinimumWidth = 16
 
        'Zwei Bitmaps für die Icon-Spalte erstellen
        nodate = New Bitmap(16, 16)
        Using g As Graphics = Graphics.FromImage(nodate),
            pn As New Pen(Color.White)
            g.Clear(Color.Red)
 
            g.DrawLine(pn, New Point(0, 0), New Point(16, 16))
            g.DrawLine(pn, New Point(16, 0), New Point(0, 16))
        End Using
 
        dateok = New Bitmap(16, 16)
        Using g As Graphics = Graphics.FromImage(dateok),
            pn As New Pen(Color.Black)
            g.Clear(Color.Green)
            g.DrawLine(pn, New Point(0, 0), New Point(16, 16))
        End Using
 
    End Sub
 
 
    Private Sub dgv_CellPainting(sender As Object,
        e As DataGridViewCellPaintingEventArgs) Handles dgv.CellPainting
 
        If (e.RowIndex >= 0 And e.RowIndex < bs.Count) 
            AndAlso e.ColumnIndex = 1 Then
 
            'Gebundene Datatable-Zeile casten
            Dim r As DataRow = DirectCast(bs(e.RowIndex), DataRowView).Row
 
            'Icon-Zelle zeichnen
            e.PaintBackground(e.CellBounds, True)
 
            'Icon in der Zelle zentrieren
            Dim lft As Integer = 
                e.CellBounds.Left + (e.CellBounds.Width - 16) \ 2
            Dim tp As Integer = 
                e.CellBounds.Top + (e.CellBounds.Height - 16) \ 2
 
            'Icon-Spalte abhängig vom Eintrag in der Date-Spalte zeichnen
 
            If IsDBNull(r("Date")) Then
                e.Graphics.DrawImage(nodate, lft, tp)
            Else
                e.Graphics.DrawImage(dateok, lft, tp)
            End If
 
            'Icon-Zelle als bearbeitet melden
            e.Handled = True
        End If
    End Sub
End Class