The main goal in the power system is to transmit the power in a more economical way with high power quality and power factor, having a smaller possibility of system collapse or failure. Operation of power system network is going complex day by day and insecure with higher power flows without adequate control. Renewable energy when connected to the power grid can invite a lot of new problems and challenges. The output power of the wind generator is greatly affected by the variable nature of the wind speed which can cause power quality issues while integrating it to the grid network. The massive growth of interconnected power systems due to increasing demand for electrical energy has given rise to numerous challenges. These problems include power swings, oscillations, sudden change in the load, loss of synchronism, blackouts, system faults that occur due to dynamics in long transmission lines of interconnected systems and long distance between load and generation points Those phenomenon causes power system problems of transient instability and has resulted power system collapse in many countries including Ethiopia. The research is inspired by the need of automating power system transient stability control by outlining the distinguishing features of the four FACTS devices for Transient Stability Enhancement by determining appropriate locations and sizes of the FACTS devices and their compensation properties. In these circumstances, Flexible Alternating Current Transmission System (FACTS) controllers such as IPFC, SSSC, STATCOM and UPFC have been improved transient stability thus enhance overall system stability during disturbances. Alongside the property of fast control of active and reactive power in power system, SSSC, STATCOM, IPFC and UPFC devices also play an additional role in transient stability enhancement as well as in damped power system oscillations and therefore play vital in system stability control. This research focuses on the specific, comparative performances of introducing the four FACTS devices in the test system have been analyzed and can be used a basis that can be generalized to all other networks. It goes further to look at the effect of single compensation device (SSSC, STATCOM) and double compensation devices (UPFC and IPFC) in the Transient Stability Enhancement, loss reduction, damped power system oscillation and voltage profile support of the combined case study of interconnection of Adama II wind farm to the modified IEEE 14-bus test system model using MATLAB/PSAT have been analyzed and compared the effect without FACTS device under faulty conditions. The overall test systems with individually SSSC, STATCOM, IPFC and UPFC placement results significant transient stability enhancement and xv have been damped the system oscillations of the multimachine and reduced the oscillations transient period. Keywords- FACTS, MATLAB/PSAT, SSSC, STATCOM, UPFC, IPFC, Transient Stability