Dwarf spheroidal galaxies (dSphs) are promising targets for the gamma-ray dark matter (DM) search. In particular, DM annihilation signal is expected to be strong in some of the recently discovered nearby ultra-faint dSphs, which potentially give stringent constraints on the $\mathcal{O}(1)$ TeV WIMP DM. However, various non-negligible systematic uncertainties complicate the estimation of the astrophysical factors relevant for the DM search in these objects. Among them, the effects of foreground stars particularly attract attention because the contamination is unavoidable even for the future kinematical survey. In this article, we assess the effects of the foreground contamination on the astrophysical $J$-factor estimation by generating mock samples of stars in the four ultra-faint dSphs and using a model of future spectrographs. We investigate various data cuts to optimize the quality of the data and apply a likelihood analysis which takes member and foreground stellar distributions into account. We show that the foreground star contaminations in the signal region (the region of interest) and their statistical uncertainty can be estimated by interpolating the foreground star distribution in the control region where the foreground stars dominate the member stars. Such regions can be secured at future spectroscopic observations utilizing a multiple object spectrograph with a large field of view; e.g. the Prime Focus Spectrograph mounted on Subaru Telescope. The above estimation has several advantages: The data-driven estimation of the contamination makes the analysis of the astrophysical factor stable against the complicated foreground distribution. Besides, foreground contamination effect is considered in the likelihood analysis.