A gratuity analyzing computing device and method are provided. The computing device may include a receiver to receive transaction data of a plurality of merchants, wherein the transaction data includes authorization transactions and clearing transactions, a calculator to match a plurality of authorization transactions with a plurality of clearing transactions, respectively, and calculate gratuity amounts for the plurality of matched transactions, an analyzer to select at least two merchants, generate tip data for each selected merchant, the tip data for a respective merchant being generated based on gratuity amounts of matched transactions that correspond to the respective merchant, and rank the at least two merchants based on a comparison of the generated tip data of the at least two merchants with respect to each other, and a transmitter configured to output the rank and the tip data of the at least two merchants to a user.