Purpose: To assess the repeatability and accuracy of three dental color-matching devices under standardized and freehand measurement conditions. Materials and methods: Two shade guides (Vita Classical A1-D4, Vita; and Vita Toothguide 3D-Master, Vita), and three color-matching devices (Easyshade, Vita; SpectroShade, MHT Optic Research; and ShadeVision, X-Rite) were used. Five shade tabs were selected from the Vita Classical A1-D4 (A2, A3.5, B1, C4, D3), and five from the Vita Toothguide 3D-Master (1M1, 2R1.5, 3M2, 4L2.5, 5M3) shade guides. Each shade tab was recorded 15 continuous, repeated times with each device under two different measurement conditions (standardized, and freehand). Both qualitative (color shade) and quantitative (L, a, and b) color characteristics were recorded. The color difference (ΔE) of each recorded value with the known values of the shade tab was calculated. The repeatability of each device was evaluated by the coefficient of variance. The accuracy of each device was determined by comparing the recorded values with the known values of the reference shade tab (one sample t test; α = 0.05). The agreement between the recorded shade and the reference shade tab was calculated. The influence of the parameters (devices and conditions) on the parameter ΔE was investigated (two-way ANOVA). Comparison of the devices was performed with Bonferroni pairwise post-hoc analysis. Results: Under standardized conditions, repeatability of all three devices was very good, except for ShadeVision with Vita Classical A1-D4. Accuracy ranged from good to fair, depending on the device and the shade guide. Under freehand conditions, repeatability and accuracy for Easyshade and ShadeVision were negatively influenced, but not for SpectroShade, regardless of the shade guide. Conclusion: Based on the total of the color parameters assessed per device, SpectroShade was the most reliable of the three color-matching devices studied.