Visual Basic Random Number

I'm trying to create a random number generator (lottery). I have the random numbers generating, but I want to loop through the numbers that are checked in my CheckedListBox. It returns my last number checked, but not the others. Any suggestions?

Public Class Form1
    Private Sub Form1_Load(sender As Object, e As EventArgs) Handles MyBase.Load

    End Sub

    Private Sub Button1_Click(sender As Object, e As EventArgs) Handles Button1.Click
        Dim number1 As Integer
        Dim number2 As Integer
        Dim number3 As Integer
        Dim number4 As Integer
        Dim number5 As Integer
        Dim lottoPick As Integer = 0
        Dim i As Integer
        For i = 0 To LotteryBox.Items.Count - 1
            If (LotteryBox.GetItemChecked(i) = True) Then
                lottoPick = lottoPick + 1
                LabelOutput.Text = (LotteryBox.Items(i))
            End If

            Randomize()
        '     The program will generate a number from 0 to 99                
            number1 = Int(Rnd() * 99) + 1
            number2 = Int(Rnd() * 99) + 1
            number3 = Int(Rnd() * 99) + 1
            number4 = Int(Rnd() * 99) + 1
            number5 = Int(Rnd() * 99) + 1
        Next
        LabelOutput.Text += number1.ToString() + " " + number2.ToString() + " " + number3.ToString() + " " + number4.ToString() + " " + number5.ToString()
    End Sub
End Class