This book constitutes the refereed proceedings of the 14th International Conference on NII Testbeds and Community for Information Access Research, NTCIR 2019, held in Tokyo, Japan, in June 2019. The 15 full papers presented in this book were carefully reviewed and selected from 55 submissions.This NTCIR 2019 proceedings was structured in the following topics: lifelog search; open live test for question retrieval; QA lab for political information; short text conversation; we want web; and fine-grained numeral understanding in financial tweet.