Sub Main()
  Dim liste As New List(Of String)
  liste.Add("Hallo 1")
  liste.Add("Hallo 100")
  liste.Add("Test 5")
 
  liste.Sort(AddressOf MyStringComparison)
 
  For Each item In liste
    Console.WriteLine(item)
  Next
End Sub
 
Function MyStringComparison(ByVal s1 As String, ByVal s2 As String) As Integer
  Dim parts1() As String = s1.Split(" "c)
  Dim parts2() As String = s2.Split(" "c)
 
  Dim firstComparisonResult As Integer = parts1(0).CompareTo(parts2(0))
 
  If firstComparisonResult = 0 Then
    ' Erste Teil ist gleich - jetzt nach Zahlen sortieren
    Dim n1 As Integer = Integer.Parse(parts1(1))
    Dim n2 As Integer = Integer.Parse(parts2(1))
 
    Return n1.CompareTo(n2)
  Else
    Return firstComparisonResult
  End If
End Function

Ralf