pokeshipping:January 14, 1999: Ash loses to Ritchie in the Indigo League, ending his first League to
pokeshipping:January 14, 1999: Ash loses to Ritchie in the Indigo League, ending his first League tournament in the Top 16September 15, 2019: Ash beats Gladion in the Alola League final and becomes Alola’s first League Champion -- source link