You don't need a loop.
Sub Win_Loss()
Dim RND_Array() As Variant
Dim n As Integer
RND_Array = Application.Sequence(1, 100, 1, 1)
RND_Array = WorksheetFunction.SortBy(RND_Array,
WorksheetFunction.RandArray(RND_Array), True)
For n = 1 To 100
Debug.Print RND_Array(n)
Next n
End Sub