Because you asked, I had a two year old and five first year pineapple plants that were rooted. The old one wintered in a 5 gallon bucket and the other five spent their winter in coffee cans, all in the greenhouse.
I left some soil on the roots and wrapped the root ball in sphagnum moss. It made it easy to keep moist.
I have been planting them out in beds and this is what they look like when I remove them.
The roots amaze me after they overwintered like that.
This was the second year I dug the large one up, overwintered and replanted it. Only mistake I made this year was setting it out before the cold was over. It looks rather ugly. I was going to try to make it bloom this summer.
As they grow larger overwintering is definitely an issue.