Congratulations, you have a Y2K bug.
The documentation for this behavior starts with the Custom Date and Time Format strings, which includes a description of the yy format specifier. Specifically, we have this excerpt:
In a parsing operation, a two-digit year that is parsed using the "yy" custom format specifier is interpreted based on the Calendar.TwoDigitYearMax property of the format provider's current calendar.
Follow that to the Calendar.TwoDigitYearMax documentation and we find this:
This property allows a 2-digit year to be properly translated to a 4-digit year. For example, if this property is set to 2029, the 100-year range is from 1930 to 2029. Therefore, a 2-digit value of 30 is interpreted as 1930, while a 2-digit value of 29 is interpreted as 2029.
The initial value of this property is derived from the settings in the regional and language options portion of Control Panel.
If you only have two digits for the year you're gonna need to guess at the tipping point between the current and previous or current and next centuries. Microsoft made their guess, but also chose to make it configurable, where different systems may have it configured different ways. This implies it's dangerous to rely on two-digit year values, as we've known since before 1999. Since 1999, no one sane uses two digits for the year anymore.
As a side note, it's been some time since this was first decided; it's probably past time for Microsoft to update that default guess (maybe 2079, or a new approach entirely, perhaps based on an offset from the current year). Unfortunately, it's a statistical certainty there are programs out there which rely on the default not changing, such that it's difficult for Microsoft to update this. It would cause what they call a "breaking change", and they are pretty good about avoiding doing that to people... though there is some discussion on changing this for .Net 8.
This situation is therefore likely to start coming up more often in the near future, and having found my way here because it indeed had come up in another place I felt it worthwhile to add a more-recent answer to this older question. There's nothing really new in this answer, except to confirm the situation hasn't (yet) changed. Maybe a Windows 11 release will have a new default?