This paper reports the results of dental mesowear and microwear analyses of bovid and cervid specimens recovered from Late Pleistocene to Middle Holocene deposits of Braholo Cave and Song Terus in Eastern Java. The aim is to infer ungulate dietary traits from dental wear signatures and gain insights regarding the paleoenvironment of the region during the last 25,000years, a period of drastic climatic fluctuations. We considered three cervid (Rusa, Axis and Muntiacus muntjak) and two bovid (Bubalus and Bos javanicus) taxa in the analyses. Results from both cave sites suggest that the Pleistocene-Holocene transition was accompanied by expansion of rainforests as evidenced by the predominance of species that had a browsing or browse-dominated mixed diet. However some of the taxa examined exhibited strong grazing signatures indicative of the continued presence of patches of grasslands up to the Mid-Holocene. Dental wear signatures of specimens from layers dating to the Last Glacial Maximum (LGM) suggest a mosaic environment dominated by grasslands. In Braholo Cave, we observed discrepancies between the mesowear and microwear signatures in specimens dating to the LGM and we take this as evidence of seasonality during this period. The results of the study provide important information on the environments encountered by the hunter-gatherer communities that lived in East Java in periods of climatic change.