Contingency Analysis can provide a powerful insight into potential operational emergencies if the real-time analysis is extended into near future. Predictive look-ahead analysis can take advantage of forecasted loads and generation, scheduled outages, and transmission dynamic ratings based on a weather forecast. This paper proposes to use simple estimate of outage probability in the predictive contingency analysis. In real time, the probability of outage is estimated using line loading and extreme weather conditions factor. For evaluation of each contingency, risk index presented as a product of severity and the contingency's normalized probability. Monitoring of projected near-term risks provides enhanced assessment of the contingency trends developing in the network. The look-ahead analysis becomes even more vital in case of quickly changing adverse weather conditions. It is proposed to perform "(N-X)" contingency analysis on high intensity storm area and tracking risk index for all contingencies.