Due to errors and tooth surface wear of herringbone gear is inevitable. And tooth surface modification is the key technology to improve gear performance. Therefore, this paper studies the influence of tooth surface uneven wear and modification on herringbone gear pair's meshing and dynamic characteristics with errors. Firstly, herringbone gear pair meshing characteristic analysis model based on discrete tooth surface is established. Secondly, herringbone gear pair bending-torsion coupling dynamic characteristic analysis model considering friction is established, and the dynamic frictional force analysis process is given. Thirdly, combined with Archard's wear theory, the tooth surface uneven wear amount is obtained. The tooth surface uneven wear amount is substituted into meshing matrix as a tooth surface deviation. Finally, the meshing and dynamic characteristics of herringbone gear pair considering tooth surface wear and modification are studied by using the established analysis model of meshing characteristics and dynamic characteristics. The calculation results show that without tooth surface modification, tooth surface wear will deteriorate the meshing and dynamic characteristics rapidly. However, reasonable tooth surface modification can effectively improve meshing and dynamic characteristics of gear pair, so that the gear pair can still maintain stable transmission under wear condition.