Estonia, which gained its independence in 1991, has carried out studies to create a digital citizen by using blockchain technology. Singapore, which is located in the southernmost part of the Asian continent and is poor in terms of natural resources, but is now an important trade center in the world, has shown a successful digital transformation performance. In this respect, these countries have been chosen as examples worth examining. Answers were sought to the questions of what kind of digital transformation Estonia and Singapore are going through and what practices that can inspire other cities in this transformation that took place in a short time. In Estonia, especially in Tallinn, projects have been carried out for the smart economy, smart mobility, smart environment, smart people, smart governance and smart life components of the smart city. Estonia's prominent smart and digital projects; contactless mobile payment, autonomous vehicle, 3D Urban Information Model, SmartEnCity Initiative, digital signature, mobile identity card, e-residence, DigiDoc, e-cabinet, e-law, e-tax, e-school, online voting, x- road data layer is the Telliskivi Loomelinnak Transformation Project. Smart projects realized by Singapore are; Lab on Wheels and SkillsFuture programs, HealthHub, OneService, SafeEntry, MyTransport.SG mobile apps, Auto Rider Autonomous Vehicle and 3D printing center. The main purpose of the study is to make a comparative evaluation on the projects developed by identifying smart or digital applications realized in Singapore and Estonia. In the study, the case study method, which is one of the qualitative research methods, was used.