It will not enter your if statement because e.Key only references the most recently pressed key, so it cant be equal to 2 different keys at once.
Try this instead(if i understand you correctly)
Put a label in ti your form and see the outcome..
private List<Keys> pressedKeys = new List<Keys>();
private void Form1_KeyDown(object sender, KeyEventArgs e)
{
pressedKeys.Add(e.KeyCode);
printPressedKeys();
}
private void Form1_KeyUp(object sender, KeyEventArgs e)
{
pressedKeys.Remove(e.KeyCode);
printPressedKeys();
}
private void printPressedKeys()
{
label1.Text = string.Empty;
foreach (var key in pressedKeys)
{
label1.Text += key.ToString() + Environment.NewLine;
}
}