C# Generate 5 random times between 08:20:00 and 08:29:59

I'm needing to generate 5 random times between 08:20:00 and 08:29:59.

These times need to be added into the top text boxes from left to right.

I'm currently doing it with this code:

private void Button1_Click(object sender, EventArgs e)
{
    listBox1.Items.Clear();
    Random random = new Random();
    TimeSpan start = TimeSpan.FromHours(08.20);
    TimeSpan end = TimeSpan.FromHours(08.30);
    int maxMinutes = (int)((end - start).TotalMinutes);

    for (int i = 0; i < 5; ++i)
    {
        int minutes = random.Next(maxMinutes);
        TimeSpan t = start.Add(TimeSpan.FromMinutes(minutes));
        listBox1.Items.Add(t);
    }
}

And this is what it looks like.

Currently, it's not generating them between the time frame and it's also not including seconds which is critical. I also need a solution to add them into their slots.

1st generated needs to go into monday_In, 2nd needs to go into tuesday_In, 3rd needs to go to wednesday_In, 4th needs to go to thursday_In, 5th needs to go to friday_In

Any ideas on how to do this?