Make sure to delete the old image and empty Photos trash before importing the new image with edited metadata.
Anyway, your exiftool output is ambiguous because it does not list tag groups and other useful info. It is best to use these options when checking tags: show duplicate tags (-a), what groups they belong to (-G1) and actual tag names (-s). Actual tag names like 'DateTimeOriginal' are used when writing tags instead those maybe more human readable corresponding names like 'Date/Time Original' without -s option.
https://exiftool.org/faq.html#Q3
So: post the output of this command for that 14-old.tif:
exiftool -a -G1 -s -api RequestTags=FileCreateDate -Time:All 14-old.tif
It seems Photos grabs incorrect 2020 date for that .tif from incorrect 'IPTC:DateCreated' and 'IPTC:TimeCreated' tags which sometimes Photos might do instead importing date from the correct 1990 EXIF tag:
So it seems you might be a victim of the old Monterey-Sequoia Photos "IPTCDigest is not current" flaw:
With such images Photos, Preview and Finder preview erroneously grab the date from 'IPTC:DateCreated' and 'IPTC:TimeCreated' instead using 'ExifIFD:DateTimeOriginal' (luckily usually those dates are the same). Photos also displays the time as "0.00" if IPTC:TimeCreated is missing and the IPTCDigest is out-of-sync:
exiftool -a -G1 -s -ExifTool:Warning -File:CurrentIPTCDigest -Photoshop:IPTCDigest image.jpg
[ExifTool] Warning : IPTCDigest is not current. XMP may be out of sync
[File] CurrentIPTCDigest : 8a2526af49e0181dc6b0fcd563517484
[Photoshop] IPTCDigest : a44c6491b26004f85a9ab6516deb2a53
As a test I wrote the correct 2000 year date with 'AllDates' shortcut to EXIF (and same name XMP) 'DateTimeOriginal', 'CreateDate' and 'ModifyDate' (as well as to the less important file dates), and deliberately wrote incorrect dates to the two IPTC datetime tags as 1977 or 1987:
exiftool -a -G1 -s -api RequestTags=FileCreateDate -Time:All image.tif
[MacOS] FileCreateDate : 2000:01:01 12:00:00+02:00
[System] FileModifyDate : 2000:01:01 12:00:00+02:00
[ExifIFD] DateTimeOriginal : 2000:01:01 12:00:00
[ExifIFD] CreateDate : 2000:01:01 12:00:00
[IFD0] ModifyDate : 2000:01:01 12:00:00
[XMP-xmp] CreateDate : 2000:01:01 12:00:00
[XMP-xmp] ModifyDate : 2000:01:01 12:00:00
[XMP-xmp] MetadataDate : 2024:11:01 12:41:53+02:00
[XMP-xmpMM] HistoryWhen : 2024:11:01 12:38:48+02:00
[IPTC] DateCreated : 1977:01:01
[IPTC] TimeCreated : 12:00:00+02:00
[IPTC] DigitalCreationDate : 1987:01:01
[IPTC] DigitalCreationTime : 12:00:00+02:00
[ICC-header] ProfileDateTime : 1998:02:09 06:49:00
[Composite] DateTimeCreated : 1977:01:01 12:00:00+02:00
[Composite] DigitalCreationDateTime : 1987:01:01 12:00:00+02:00
I then imported that .tif to Photos and, sure enough, Photos IMHO incorrectly grabs the date from incorrect IPTC:DateCreated and IPTC:TimeCreated instead using the correct EXIF tag (with G1 exiftool displays ExifIFD:DateTimeOriginal specific location and with G0 EXIF:DateTimeOriginal general location).
It is possible to sync those out-of-sync IPTCDigests with the first command below but nowadays the best fix is to delete Photoshop:IPTCDigest with the latter command:
exiftool -m -P -overwrite_original -Photoshop:IPTCDigest=new image.jpg
exiftool -m -P -overwrite_original -Photoshop:IPTCDigest= image.jpg
So: try if deleting Photoshop:IPTCDigest fixes the date Photos imports. Then those incorrect IPTC dates should not matter. But if DateTimeOriginal is correct, you could copy that to those IPTC tags with:
exiftool -m -overwrite_original '-DateCreated<DateTimeOriginal' '-TimeCreated<DateTimeOriginal' '-DigitalCreationDate<DateTimeOriginal' '-DigitalCreationTime<DateTimeOriginal' image.tif
Or, if DateTimeOriginal is correct, delete those pesky IPTC date tags with:
exiftool -m -overwrite_original -DateCreated= -TimeCreated= -DigitalCreationDate= -DigitalCreationTime= image.tif