Background/Objectives Light-assisted in-office whitening procedures are widely used in clinical practice; however, comparative clinical data remain limited, particularly when evaluated using objective outcome measures. This exploratory pilot randomized clinical trial aimed to assess the immediate objective performance of two light-assisted in-office whitening protocols using standardized digital spectrophotometry. Materials and Methods Twelve healthy adult participants (18–45 years) presenting extrinsic or mixed-type tooth discoloration (baseline shade VITA A3 or darker) were randomly allocated into two parallel groups (n = 6 each). One group received whitening with a 35% hydrogen peroxide gel activated by a diode laser device, while the other group underwent whitening with a 25% hydrogen peroxide gel activated by an LED-based device. Tooth color was measured before and immediately after treatment using a digital spectrophotometer (VITA Easyshade V, VITA Zahnfabrik, Bad Säckingen, Germany), and color differences (ΔE) were calculated based on CIE L*a*b* coordinates. Statistical analysis was performed using the Mann–Whitney U test. Results: Both light-assisted interventions resulted in clinically perceptible whitening outcomes (ΔE > 3.3). The LED-assisted group showed a slightly higher mean ΔE value (11.62 ± 5.93) compared with the laser-assisted group (10.96 ± 3.27); however, the difference was not statistically significant (p = 0.818). Given the limited sample size, the study was not powered for definitive comparative inference. No adverse events were recorded. Conclusions: Within the limitations of this exploratory pilot randomized clinical trial, both light-assisted in-office whitening protocols produced immediate clinically perceptible color changes. Although no statistically significant difference was detected, the limited sample size precludes definitive conclusions regarding relative efficacy. Larger, adequately powered randomized studies incorporating longitudinal follow-up and patient-reported outcomes are required to confirm these preliminary findings.