My mom is 82. Maybe ten years ago she got a bad case of pneumonia; she'd had it before, but this one went on for a very long time. Finally, they got it under control; but she has to stay on antibiotics for the rest of her life. Whatever bug was involved apparently has a little home it made in her lungs, and they can't knock it out of there. If she goes off the antibiotic for a couple of weeks, the pneumonia starts to come back.
So yes, it's possible if your immune system is weak and/or the bug is strong. Moreover, viral infections like the flu often lead to secondary infections caused by a combination of low resistance and respiratory blockages; sinus infections are the most common. That's why sometimes you get the flu, get better, and then get worse again. The "relapse" is actually a secondary bacterial infection of some kind. I once got the flu and was sick for a solid month; I started to get better twice, and then relapsed. I didn't think antibiotics would work on the flu, but somebody finally explained secondary infections to me and I got a prescription. Two days later I felt normal. God knows how long the cycle would have gone on without the pills.
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