The aim of this research is to determine the relationship between work values and work enjoyments of teachers from X and Y generations in relation to their gender, seniority and generation. The study was designed with single and correlational survey models. A total of 28501 elementary and public secondary school teachers from Ankara were represented by 381 participants in the sampling from nine central districts of Ankara. "Work Values Scale " was developed by the researchers and "Work Enjoyment Scale " was translated to Turkish. Results indicated that Y generation teachers more care about each dimension of work values than the X generation teachers. Teachers have a moderate work enjoyment level. Female teachers attach more importance to self-improvement, external rewards than male teachers. Teachers with seniority of 21 years or more enjoy more than the teachers with seniority 6-10 years. The relationships between extrinsic rewards and work enjoyment levels of the X generation teachers were found to be positive and low whereas the other dimensions of work enjoment levels of X generation teachers were found to be positive and medium level. Since Y generation refuses to count in place and expect continuous improvement during their career pathways, it would be appropriate to enrich career opportunities for Y generation teachers.