The continuity of transformer operation is very necessary for utilities to maintain a continuity of power flow in networks and achieve a desired revenue. Most failures in a transformer are due to the degradation of the insulating system, which consists of insulating oil and paper. The degree of polymerization (DP) is a key detector of insulating paper state. Most research in the literature has computed the DP as a function of furan compounds, especially 2-furfuraldehyde (2-FAL). In this research, a prediction model was constructed based on some of most periodical tests that were conducted on transformer insulating oil, which were used as predictors of the insulating paper state. The tests evaluated carbon monoxide (CO), carbon dioxide (CO2), breakdown voltage (VBD), interfacial tension (IF), acidity (ACY), moisture (M), oil color (OC), and 2-furfuraldehyde (2-FAL). The DP, which was used as the key indicator for the paper state, was categorized into five classes labeled 1, 2, 3, 4, and 5 to express the insulating paper normal aging rate, accelerating aging rate, excessive aging danger zone, high risk of failure, and the end of expected life, respectively. The classification techniques were applied to the collected data samples to construct a prediction model for the insulating paper state, and the results revealed that the fine tree was the best classifier of the data samples, with a 96.2% prediction accuracy.