A system for reconciling pharmacy payments may include pharmacy devices, each associated with a respective pharmacy generating respective pharmacy claims, and provider payment devices, each generating a paper log of payment data associated with payment of the pharmacy claims. A pharmacy payment reconciliation device may generate and store electronic historical records of payment data based upon user entry from the paper log of payment data, and determine a predicted claim for a current pharmacy payment based upon the stored electronic historical records. The pharmacy payment reconciliation device may display the predicted claim in a field for user entry of a corresponding current payment, and accept user confirmation or correction of the predicted claim in the field for user entry of the corresponding current payment to thereby assist the user in entry from the paper log of payment data.