As tabletop games are ported to digital versions to increase their accessibility, the expected User Experience (UX) might be degraded in the transition. This paper aims to understand how and why playing tabletop games differentiates depending on the platform. Seven tabletop games have been chosen from different genres with an official digital adaptation. Our approach has been to do a comparative analysis of both versions followed by a user study to analyze and measure the UX differences, measuring five key factors, Usability, Engagement, Social Connectivity, Aesthetics, and Enjoyment. Our results indicate that games that rely on imperfect information offer a much higher social connectivity and engagement when played around a table. Meanwhile, games relying on tile-placement offers higher usability and engagement when played digitally due to the assistance provided by the game. However, the physical versions got, in general, a higher rating than the digital versions in all key factors except slightly in the usability. Physical versions are the preferred options, but the digital versions' benefits, such as accessibility and in-game assistance, makes them relevant for further analysis.