Answer by Peter Baskerville:

In the 500+ years of bookkeeping's evolutionary history “Dr” was first used as an abbreviation for the personalised concept of “debtor” but has since morphed over the centuries into the convention of applying it to the abstract concept of "debit".
This issue also bothered me greatly when I was first introduced to bookkeeping and accounting, and luckily it also bothered Professor Richard Sherman at Rutgers University. He did extensive investigations into this issue and provided the answer in this rather lengthy academically researched article – Where’s the “r” in Debit?
Now I know that some teachers today put student minds to rest by explaining that the 'Dr' is an abbreviation for 'Debit Record' and the 'Cr' is an abbreviation for 'Credit Record', but history doesn't necessarily support this theory.
In the early days of my investigation I was happy to settle for the fact that as our English texts for accounting/bookkeeping were translated from original works written in Latin, that in translating the Latin words debere and credere to the English words debit and credit, the English translators must have simply kept the "Dr" and "Cr" abbreviations from the Latin … because at least there is an 'r' in the Latin debere.
But Professor Richard Sherman's research didn't support this theory either because the original Latin text Summa de Arithmetica, Geometria, Proportioni et Proportionalita (translated: Everything About Arithmetic, Geometry, Proportions and Proportionality) written by the Italian mathematician Luca Pacioli in 1494, did not contain the words debere and credere or use "Dr" or "Cr" at all, but rather used the terms Per ("for") and A ("to").
Professor Richard Sherman believes that he has found the answer to the "r" in "debit" riddle and supports it with some vagarious and robust research:
Now the mystery is solved — “Dr” is an abbreviation for “debtor”; “Cr” is short for “creditor.”
After fully researching the issue, Professor Richard Sherman acknowledges that using the “Dr” for "Debit" makes little sense to us today, but explains that such is the result of terms and symbols that morph in their meaning in all systems with centuries of use.

Why is the bookkeeping abbreviation for debit 'dr'?