Background and Objectives: Appropriate tooth preparation is mandatory to obtain a perfect marginal fit of fixed restorations. The heavy chamfer is the most commonly used finish line, especially for minimally invasive tooth preparation. The aim of the study was to compare the width of the finish line obtained during tooth preparation performed by experienced (university lecturers) and inexperienced persons (dental students) in different working times and positions. Materials and Methods: Forty left upper-second molars were prepared on the simulator by each participant, totalizing 160 prepared teeth. A new round-end tapered diamond was used to obtain the 0.5 mm width of the heavy chamfer. The prepared teeth were photographed using a Canon D5300 camera with a macro lens attached to a tripod. The measurements were made with the Image-Pro Insight software selecting the same eight reference points. From these points, perpendicular lines were drawn above the finish line to the axial walls and the distance between the chamfer’s outer edge and the axial wall’s inner edge was measured. GraphPad Instat and NCSS Dowson Edition software were used. The statistical significance was set at p < 0.05. The mean (M) and standard deviation (SD) were calculated. The used tests: one sample t-test, ANOVA test, and Tukey–Kramer Multiple Comparisons Test. Results: Statistically significant differences were obtained according to the experience of the participant, preparation time, patient’s position, and the chamfer width on the prepared tooth different surfaces. Conclusions: Daytime or weeklong tiredness and patient position do not affect the width of the heavy chamfer prepared by experienced and inexperienced persons. The experience and the operator’s working position influence the width of the prepared finish line.