Rex,
The short answer is... yes.
The rather longer answer is you need to do some stuff before you get there. You'll want to start with the upgrade guide and find out what stops you need to make along the way for your upgrade. Once you know your stops along the path to the latest and greatest, I highly recommend you also look at the "supported platforms" for each of the versions. Along with some of the stops you need to make with JIRA, you're also going to have to start with supported versions of (the biggest one) the DB you are using as the backing store as I ran into cases where too new of a DB wouldn't work with an older JIRA.
An even bigger suggestion I might make is that (if you have the resources and/or can spin VMs for it) is to make a dev box for EACH step in the upgrade and move from one to the next. In this way you can try your upgrade/migration without having to redo stuff when (not if) it craters. Document the HECK out of every dang keystroke you make so when you get to a spectacular failure point, at least you know how you got to the last successful point and don't have to relearn it.
Finally (and learned this from one of my bigger leaps I had to make when I took over the stack here and plays into enough systems with documented steps for each upgrade step), don't make your final leap until you've managed to successfully migrate and validate data, screens, workflows, etc at least three times before you do it for real.
Even after making the "successful" final move, keep the old box around for a while so if something seems awry, you can at least see what it SHOULD be to fix the new one.
Good luck. That is a big leap to make
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