I just find it really weird that this kind of thing goes on in some schools. I went to a pretty good school (state grammar as I live in an area where the 11+ system still exists), and we have people applying to Oxbridge every year, but I can't imagine anybody was so obsessed that they would try to hide their rejection.
Out of interest (Bumblebee), how many people in your school generally apply and what proportion are accepted? I really think your school (or maybe the parents of students in the school) need to start promoting a healthier attitude about the whole thing.