In your delegate, the function
- (BOOL)textFieldShouldClear:(UITextField *)textField
is called when the users wants to clear the textfield. If you return YES and call
[textField resignFirstResponder];
the keyboard should go away. I don't know about the clearButtonMode, other than that you may want to set it early, preferably before adding the view to its superview.
edit To make sure you really resign the responder, try doing it just a little later:
[textField performSelector:@selector(resignFirstResponder) afterDelay:0.1];