It would need to be done both ways.
A 1923 student is not going to have read "The Gulag Archipelago" or "Things Fall Apart" or other works published after 1923, so would fail any modern questions which require having read those works.
But even if you look to contemporaneous 1923 literature, I strongly suspect a modern Harvard student is more likely to have read black literature from 100+ years ago than a 1923 student. (For examples see https://histlit.fas.harvard.edu/files/histlit/files/america_... with "Sample Oral Exam Questions" from a modern Harvard exam section on "Being Black After Reconstruction".)
If the 1923 student didn't have to read 75% of what modern literature courses cover, and instead read a different 75%, perhaps with a stronger emphasis on British literature, then of course a 2023 student won't test so well on a 1923 test. But then, a 1923 student wouldn't test so well on a 2023 test.
Even math has some issues. Here's a Harvard entrance exam from 1869: https://graphics8.nytimes.com/packages/pdf/education/harvard...
You can see the math part requires details that aren't taught now:
"Find the amount of £50 12s. 5d. at simple interest at 8 per cent., at the end of 5 years 2 months and 3 days."
"From 1 sq. rod 5 sq. ft. subtract 7 sq yd. 139 sq. in."
The Brits decimalized a half century ago, so kids aren't taught there are 20 shillings in a pound and 12 pennies in a shilling. Only surveyors use rods these days, and it's defined as 16 1/2 US survey feet - which is slightly smaller than the international foot defined in 1959.
Or, "Find the cube root of 0.0093". By hand. We no longer consider that something worthwhile to teach.
They aren't hard, but without that small bit of knowledge or training, modern students are very unlikely to get the right answer.
Or, "State and prove the proportion which exists between the parts of two chords which cut each other in a circle. State what proportion exists when two secants are drawn from a point without the circle." I don't know about you, but my plane geometry isn't good enough to answer that question.
That's due to post-war educational policy changes that de-emphasized classical geometry in favor of calculus.