No, my team is permanently tanking so I have some retirements almost every season.
You can have an extension twice but this is from 33 to 34 and 34 to 35 as @pcmacdaniel said.
But not from 35 to 36.
I think this is another tricky question from nik
I 'm trying to remember if there is any case from the old version or 2015 but I don't think so.
It was the same just like this latest version.