Reusable plastic sports bottles are used extensively worldwide, and little is known about the migration of chemicals from the bottles into drinking water. In this study, we investigated the chemical migration into drinking water stored for 24 h in new bottles, used bottles and bottles washed in the dishwasher. Non-target screening (NTS) by liquid-chromatography - high-resolution mass spectrometry (LC-HRMS) was performed to identify these compounds. We detected > 3500 dishwasher related compounds, with 430 showing migration even after subsequent flushing of the bottles. In addition, more than 400 plastic related compounds were detected, with high peaks for oligomers suspected to originate from the biodegradable polyester polycaprolactone, and aromatic amines, which may have been introduced as slip agents or antioxidants. These compounds have never been reported before in bottled water. Most of the identified compounds migrating out of the used bottles were plasticizers, antioxidants or photoinitiators. The presence of photoinitiators are of particular concern, due to possible endocrine disrupting effects. Furthermore, diethyltoluamide (DEET) was detected, which may have been formed from the plasticizer laurolactam. Typically, the dishwashing process enhanced the leaching of plastic related compounds, and even after additional water flushing, the average peak intensity of these compounds was only reduced by half.