Try this
[php]
Private Sub RandomCombo()
Dim I As New Random
Dim X As Integer = I.Next(0, ComboBox1.Items.Count - 1)
ComboBox1.SelectedIndex = X
End Sub
Private Sub Button1_Click(ByVal sender As System.Object, ByVal e As System.EventArgs) Handles Button1.Click
RandomCombo()
End Sub
Private Sub ComboBox1_SelectedItemChanged(ByVal sender As System.Object, ByVal e As System.EventArgs) Handles ComboBox1.SelectedIndexChanged
If ComboBox1.SelectedItem = "APPLES" Then
RandomCombo()
End If
End Sub
[/php]
Essentially create a sub to call random index,
Button press goes to sub
on item change check if it is "Apples" , if so Re roll
note : have not tested, using above theory and basic principles, if not, concept may need modification