Wind turbines constitute a sustainable and effective solution for the production of energy using wind power. Offshore wind turbines are becoming of special interest. However, their design poses great challenges, since an offshore structure is subjected to combined wind and wave dynamic loading that is characteristic of the installation site and play an important role on the fatigue failure of the wind turbine structure. One part of specific interest for the fatigue assessment of a wind turbine is the way that the transition piece is connected to monopile. Since now, grouted and bolted connections are commonly used, but their many drawbacks regarding their performance inspired Fistuca BV to invent a new type of connection, the wedge connection, in order to increase the fatigue life of the wind turbine structures and decrease simultaneously their construction and installation cost. More specifically, a basic flange with inclined planes is attached on the top of the monopile and a more complex one (fork-shaped flange) is fitted to the bottom of the transition piece. Inclined dowels are used to connect the two flanges and secure the structure. The final positioning of the dowels is achieved by applying external pressure on the back side of them, which is converted to a vertical reaction force between the two flanges through the inclined planes, acting as preload. The work that will be presented here deals with the fatigue assessment of the wedge connection, and how the presence of the preloading force may affect the fatigue life of it. A reference wind turbine and a reference location have been selected first, in order to calculate all the fatigue loads resulted on the structure due to wind and wave at the level where the wedge connection has been selected to be located (+4m above the MSL). The concept of damage equivalent loads has been applied. Damage loads due to waves have been calculated in the frequency domain, while damage loads due to wind have been handled in the time domain due to strongest non-linearities in the rotor aerodynamics. The process of damage loads’ calculation was carried out using MATLAB. Once the loads have been calculated, the 3D CAD design software of SOLIDWORKS is used to design all the components of the wedge connection and assemble them to their final position. To facilitate the design process and reduce the computational time, the flange connection is reduced to a single wedge segment, on which the highest stresses are developed. Two load cases are examined for each one of the above resulted damage loads: one with preload and another one without preload. For the purpose of this thesis, xx MPa external pressure has been applied for the final positioning of dowels in case of preload. ANSYS Workbench has been used for the finite element analysis. Nominal stresses are calculated and based on selected S-N curves for both DNV-GL codes and Eurocode 3 and by making use of the Miner’s rule, the damage and the fatigue life of the connection is calculated. The selection of the appropriate S-N curve for each load case and for each component of the connection, has been based on results from test specimens. A parametric study has been carried out as well, in order to check several parameters that may affect both the accuracy of the finite element analysis and the stress development on the connection, and as a result the damage and the fatigue life of it.