Calibration is not about how it looks to you on your screen, though it can help with that. It is about matching your screen to a standard so it looks as close as possible on your screen and any other calibrated screen. If you are printing you have a known standard to base it upon so that printer profiles will accurately match when you print.
As I understand it color calibration devices do wear out, my i1 pro suddenly made my screen look too magenta (I had not calibrated for a year or two) , the sudden change is what alerted me. If you look at the device you'll see 4 small holes and in each of these is a colour filter placed over a photo diode. It measures the apparent brightness through each filter to measure each colour patch. Older and cheaper devices use dye based filters which fade over time and if they have faded they are no longer accurate. It is also possible the photodiode sensitivity may drift which would cause a similar problem.
Newer and better quality devices use dichroic filters which are less susceptible to fading and should last longer. I now have the new i1 display which has these new filters so should last longer.
The issue with monitors not matching prints is an ongoing issue. It comes down to the fact the monitor is backlit and the paper is frontlt, the contrast range the monitor is capable of is much greater than the what any printed image is capable of. One solution suggested is to have different profiles you can load, one set with a lower contrast ratio like 200:1 and turn that on when you are soft proofing prior to printing: Here is a guide that explains this for monitors with direct hardware calibration: https://imagescience...h-spectraview-2
This is likely the reason you are getting a better match with the glossy screen, the bold image it shows pushes you to pull back on the image before printing it.