Based on high contrast images obtained with the Gemini Planet Imager (GPI), we report the discovery of two point-like sources at angular separations of $\rho\sim0.18''$ and $\rho\sim0.80''$ from the stars HD 29992 and HD 196385. A combined analysis of the new GPI observations and images from the literature indicates that the source close to HD 29992 could be a companion to the star. Concerning HD 196385, the small number of contaminants ($\sim0.5$) suggests that the detected source may be gravitationally bound to the star. For both systems, we discarded the presence of other potential companions with $m>75$ M$_{\rm Jup}$ at $\rho\sim0.3 - 1.3''$. From stellar model atmospheres and low-resolution GPI spectra, we derive masses of $\sim0.2$ - $0.3$ M$_{\odot}$ for these sources. Using a Markov-chain Monte Carlo approach, we performed a joint fit of the new astrometry measurements and published radial velocity data to characterize the possible orbits. For HD 196385B, the median dynamic mass is in agreement with that derived from model atmospheres, whilst for HD 29992B, the orbital fit favors masses close to the brown dwarf regime($\sim0.08$ M$_{\odot}$). HD 29992 and HD 196385 might be two new binary systems with M-type stellar companions. However, new high angular resolution images would help to definitively confirm whether the detected sources are gravitationally bound to their respective stars, and permit tighter constraints on the orbital parameters of both systems.