The infrared (IR) satellite remote sensing of sea surface skin temperature (SSTskin) is challenging in the northern high latitude region, especially in the Arctic because of its extreme environmental conditions, and thus the accuracy of SSTskin retrievals is questionable. Several Saildrone uncrewed surface vehicles were deployed from Dutch Harbor, Alaska, navigating through the Bering Strait to the Pacific side of the Arctic in 2019, and two of them, SD-1036 and SD-1037, were equipped with a pair of IR pyrometers on the deck whose measurements have been shown to be useful in the derivation of SSTskin with sufficient accuracy for scientific applications, providing an opportunity to validate satellite SSTskin retrievals. The accuracy of MODIS-retrieved SSTskin from both Aqua and Terra satellites is assessed by comparisons with collocated Saildrone-derived SSTskin data. The spatio-temporal criteria of MODIS-Saildrone matchups follow that the time window is within 30 min and the distance is within 10 km. However, due to the high observing frequency (1 min) of Saildrone, there can be multiple Saildrone measurements (up to 60) matched with the same MODIS pixel, and the distance-smallest one-to-one MODIS-Saildrone matchups are selected.The datasets include matchups between Aqua/Terra MODIS and two Saildrones (SD-1036 and SD-1037), and the matched data for each MODIS sensor with each Saildrone cruise have been merged into a single csv file (four csv files in total) which contains the time and geolocation information (latitude and longitude in WGS84) of both MODIS and Saildrone measurements, high quality SSTskin retrievals from both MODIS and Saildrone, subsurface temperatures (SSTdepth) from Saildrones, and other ancillary data. For the Saildrone-measured SSTdepth, sst0_sbe56 to sst6_sbe56 represent the tempertures taken by the SBE56 loggers at -0.33 m, -0.47 m, -0.81 m, -1.04 m, -1.20 m, -1.42 m, and -1.71 m; sst_sbe37, sst_ctd_rbr and sst_o2_rbr are the SSTdepth from SBE37 and RBR CTD sensors (note that an additional temperature and optical dissolved oxygen sensor attached on the RBR CTD). Missing values are given as -9999
