This work reports the results of a study on the behaviour of five sensors recently developed for oil conditions monitoring, installed in-line in an experimental test rig for lubricants. The tests were carried out on seven oils of different origins (one synthetic ester, two bio-based synthetic esters, four vegetable oils) and use (two UTTOs and five hydraulic oils), under controlled working conditions, according to a specially designed test method. At first, the study concerned the identification of the conditions for the correct sensors’ installation. Then, the tests started applying to the fluids severe work cycles intended to accelerate oil ageing. The data of viscosity, permittivity, relative humidity, electric conductivity, particle contamination, and ferro-magnetic particles provided by the sensors were compared to the results of laboratory analyses made on oil samples taken during the tests with the aim of verifying the sensors measurements accuracy and reliability and selecting the more suitable ones to in-line oil conditions monitoring, in the perspective of introducing them also in field applications, e.g., on agricultural tractors, for preventing damages due to oil deterioration, and in managing the machine maintenance.