Background: Plating of proximal phalangeal fracture is the commonly adopted fixation method. However, whether placing the implant at the dorsal or lateral aspect of the phalanx can yield a better clinical outcome is still under debate. Our study aims to compare the functional outcome of dorsal plating versus lateral plating in patients suffering from a proximal phalangeal fracture. Methods: A retrospective comparative study was performed comparing the clinical outcome of dorsal and lateral plating in proximal phalangeal fracture. Fourteen patients from our center with a total of 17 proximal phalangeal fractures (excluding the thumb) were included in this study. The total range of movement and range of movement of each finger joint together with grip strength were the main focuses of this study. Operative complications and the need for subsequent related operations were also analyzed. Results: Nine cases were treated by dorsal plating and eight cases adopted lateral plating. There was no significant difference in demographic data between the two groups with a mean follow-up period of 20.75 months. Lateral plating provided better total range of movement (dorsal plating (D): 203.9 ± 35.2 vs. lateral plating (L): 248.8 ± 23.7; p-value = 0.01) and percentage change in total range of movement (D: 79.41% ± 10.35, L: 94.47% ± 6.09; p-value < 0.01). There was less extension lag in lateral plating as evidenced by the sum of extension lag of the three finger joints being statistically significantly smaller (D: 32.8 ± 14.2 vs. L: 4.44 ± 6.2, p < 0.01). Less percentage decrease in grip strength compared with the contralateral normal hand was also noted in the lateral plating group (D: 68.17% ± 31.11 vs. L: 98.13% ± 10.88, p = 0.02). Conclusions: Based on this study, lateral plating provides better functional outcomes in terms of range of movement, extension lag, and grip strength than dorsal plating. Level of Evidence: Therapeutic, retrospective comparative study, Level III.