Very rarely. But there have been two exceptions:
Strawberry Fields Forever - The Beatles
I listened to the Blue Album on YouTube when I was just getting into them. I played this four times consecutive!
Light My Fire - The Doors
Heard it on the return flight from Germany. Upon arrival, I found it on Youtube and listened three times in a row!

Oh I listen to the same songs over and over ALL the time! Basically anything radio-friendly I play all the time.

Suit and Tie....Thrift Shop....Last Child....Satisfaction....Radioactive....

I'm definitely guilty of this, especially when I hear a really good song for the first time. It's not over and over but I'll listen to the same song quite a few times in one day.

I tend to avoid listening to a song over and over in fear of getting tired of it. Still, sometimes I can't resist. It used to be F.C.P.R.E.M.I.X. by The Fall of Troy, and more recently it was Want by Jawbreaker.

Spanish fly times a million

Yes I do this most of the time too. I listen to the same album on repeat too - I can this for up to a month without getting bored!

Oh I've developed the same fear too. I just can't help myself some times though, listening to a song over and over.

If I really really like the song then I will. Or if it has a good beat to it I will. I am so guilty of this.

I can't get enough of Sea Legs by Run the Jewels. Played it 6 times in a row last night and twice today. That hook is insane!

Shortly after I bought Surrealistic Pillow I must have listened to How Do You Feel at least 10 times in a row. I think I fell asleep to it with the earphones on and my CD player on repeat mode.