A system and method is provided that automatically annotates gameplay based on triggering events that occur during a gameplay session. The system may automatically annotate the gameplay in real-time, such as during a gameplay session associated with an electronic-sports tournament. For example, the system may obtain and parse a game log corresponding to the gameplay session, identify triggering events based on the game log, obtain an annotation rule associated with the triggering event, generate an annotation item based on the annotation rule, and cause the annotation item to be presented in association with video of the gameplay session. An annotation item may be displayed interactively such that, when selected, causes the system to take an action. The action may include obtaining additional information relating to the selected annotation item; saving, sharing, liking/disliking or commenting on the selected annotation item; removing the selected annotation item from a display, and/or other actions.