In 23.05, the Checkout history tab in the OPAC sorted by most recent checkouts first, then descending (under any current checkouts). With 24.05 and 23.11, it is sorting by oldest checkouts first, then ascending (after any current checkouts).
Authur is in the process of making those tables configurable. ( see Bug 30221 ) If we got that in it would be really easy to add a default sort order to each of those tables, including checkouts. That way librarians could choose how these initially sort.