The article presents an analysis model of the cyclical nature of restructuring at wineries as a component of the implementation of their anti-crisis restructuring process. The activity of wine industry enterprises of the Odessa region in 2005–2014 is investigated. The sequence of modeling of the crisis phenomena analysis at the researched wine industry enterprises in the Odessa region is proposed. The given model allows: to estimate the time of the start of the anti-crisis restructuring processes, to reveal the trend of the analyzed financial indicators changes; to determine the critical points that serve as an indication of the need for restructuring; to predict the enterprise’s assets values and to make appropriate management decisions, that is, scenarios for emerging from the crisis (restructuring scenarios).