As the intermediate-mass siblings of stars and planets, brown dwarfs (BDs) are vital to study for a better understanding of how objects change across the planet-to-star mass range. Here, we report two low-mass transiting BD systems discovered by TESS, TOI-4776 (TIC 196286578) and TOI-5422 (TI 80611440), located in an underpopulated region of the BD mass─period space. These two systems have comparable masses but different ages. The younger and larger BD is TOI-4776 b with 32.3−1.7+1.8MJup and 1.01 ± 0.05 RJup, orbiting a late-F star about 4.7−2.5+3.1 Gyr old in an ∼10.41 day period. The older TOI-5422 b has 28.0−1.2+1.6MJup and 0.81 ± 0.03 RJup in an ∼5.38 day orbit around a subgiant star about 7.6−2.6+2.5 Gyr old. Compared with substellar mass─radius evolution models, TOI-4776 b has an inflated radius. In contrast, TOI-5422 b is slightly "underluminous" with respect to model predictions, which is not commonly seen in the BD population. In addition, TOI-5422 shows apparent photometric modulations with a rotation period of 10.8 ± 0.5 days found by rotation analysis, and the stellar inclination angle is obtained to be I⋆=76−12+10 deg. Therefore, it is likely that TOI-5422 b is spinning up the host star and its orbit is aligned with the stellar spin axis.