In Italy, about 160 fatal accidents per year have occurred recently in agriculture, most of them involving agricultural machinery. The most frequent cause of fatal events is the tractor overturning. One of the opportunities to monitor the trend of agricultural tractors fatal overturning is a meticulous search for information on the numerous web portals, at national and local level. In fact, in their information purposes are also included the recording, practically in real time, of significant details about each fatal event, such as the place of the accident, the year, the month and the day of the week of occurring, the victim’s age, gender and nationality, etc. This article is describing the results of the monitoring of fatal tractor overturning accidents in the period of 2008–2019 in Italy. In the 12 years of the survey, 1414 fatal accidents were recorded, most of them occurring in the spring and summer months. The region with the highest cumulative number of fatal events was Tuscany (143). The majority (58.8%) of the victims were over 60, while 71.4% of accidents occurred during field work. Most (57.6%) of the tractors involved in the fatal events did not have rollover protective structures (ROPS), while 19.4% were equipped with a two-post foldable front roll-bar, which, however, was in the lowered position at the time of the accident. In most cases, the tractors involved were obsolete and in poor maintenance conditions, and did not comply with general and specific laws on work safety. To improve the situation, the introduction of the tractor training certificate for the drivers and the periodical inspection for tractors, as well as the issuing of significant financial supports to encourage the replacement of the old models with modern more safe models, are the most effective actions to be put into practice.