There was a takedown model of the Savage 99 made in some calibers.
Could a takedown model be the rifle you have and The barrel is not properly installed, Or could it be the wrong barrel for that particular rifle action. Is there any matching or unmatched numbers on the barrel and action. The .38-55 is a rimmed case, The headspace should be off the rim. Or the rifle was shot with a plugged barrel of Snow or Water and shoved the locking section on the back of the bolt out of specs. I would take it to a experienced gunsmith who works on 99 Savage for a checkup.
See the same problem on my Son's Savage 99 in 30-30 , round barrel. It was left to him by his Maternal Grandfather who had a penchant for always loading maximum loads listed in his reloading manual (of no matter , but I think RCBS). He wanted maximum shock value for a quick kill.
We were firing Winchester factory rounds, not Ira Tom's max handloads. And the primers were backed out. Anyway, we took it to a gunsmith , really good one, who wanted to reset the headspace. I thought taking one turn off would have corrected it, but he ( the smith) wanted to take quite a bit more. Then the forearm wouldn't fit as it should. My son didn't want to do that. He wants the rifle to be just as his Granddad touched it last. So it's been a safe queen. We contemplated just neck sizing so the rounds would fit the chamber , much like is done for belted mags. But just never got around to that.