He probably did have some type of the flu at least one of those times, but it would be extremely unlikely that he had H1N1 twice.
A few years ago both my kids and dh came down with strep, they all had positive strep tests. That Friday night I got hit with a sudden high fever and sore throat, before long I had tons of white puss bubbles on my throat. I had two options, go to the ER or see if I had any refills on antibiotics (the doctor I had at the time always wrote one refill for every prescription he gave me. I'm not sure why but I think it was because I had trouble swallowing pills and half of them would often end up wasted and I'd need another bottle.) So Saturday I called the pharmacy and they said I had a refill of z-pack, so I had that filled (normally I would not take antibiotics without seeing a doctor first but it was pretty obvious what was wrong) I still made an appointment Monday and saw the nurse practitioner. When she examined me she said it was probably the flu, because that's what was going around. I told her that everyone in the house had strep. She couldn't do a strep test because I was already on antibiotics but she said if it was strep I should already be better (it was just less than 48 hours since starting antibiotics) so it must be the flu. She finally did a nasal swab and it was negative. Still she insisted I had the flu and should stop taking the antibiotics
The kicker... the week before my mom got sick and went to see her, she had a positive strep test and was put on antibiotics, four days later she was still sick so she went back in. The nurse told her she needed to give the meds a chance to work. But apparently had I had strep I should have been better in less than 2 days.
My point being, I think whenever there's an outbreak of the flu, some health care professionals are just as guilty of classify all "flu-like" symptoms as the flu, unless proven otherwise.
Like I said in my earlier post, if it was influenza both those times, it's most likely that one of them was probably the seasonal flu.
One or both of them could have also been one of the many viral or bacterial infections that can cause "flu-like" symptoms. Like I also said in my earlier post even though H1N1 is going around the campus, it almost certain that several other illnesses are too.....it's college (aka...a germ factory)