Increasing loads, ageing of materials as well as environmental change make the issue of fatigue damage critical on bridges, especially in the case of old steel or iron structures. The assessment of the fatigue loads on specific elements of these assets can be carried out from on-field strain measurements with the application of classical methods involving rainflow cycle counting and the use of Palmgren-Miner's rule. However, such a fatigue assessment suffers of significant uncertainties about the real fatigue damage ratio and the consecutive residual fatigue life. A new probabilistic method for the fatigue assessment is proposed, as the result of a joint research by OSMOS Group and the Ecole des Ponts. The theoretical background of the method is described, involving a probabilistic formulation of Miner's rule and the use of a Weibull-Basquin model to describe the health of structural elements. Real field case studies are presented, on two historical iron truss road bridges in France, with a dataset of more than 18 months of continuous strain measurements used for the fitting of the probabilistic model of fatigue loads. The incidence of the quantity of data and of the number of sensors used for the analysis is discussed, along with the conclusive results concerning the probabilistic description of the residual fatigue life.