Grupo del Oeste is considered the most awarded group of the Iloilo Paraw Regatta Festival’s Sinamba sa Paraw Regatta in which the researchers are members. Our four championship trophies (2008, 2009, 2011, and 2012), and runner-up awards (third place in 2010 and first runner-up in 2013), made Grupo del Oeste the group to beat. Taken from the idea of what made and kept Grupo del Oeste win in the competitions, this interpretivist study aimed to look into our experience sand perceptions of the competition. Data were gathered through written reﬂections and verified through one-on-one interviews. The findings of the study revealed salient points on the reasons that made us win and the challenges we met to keep winning. Definitions of participation that we realized on our road to winning along with valuable skills and essential attitudes that we gained from our participation with Grupo del Oeste were also highlighted. Furthermore, we also identified our contribution in promoting the Ilonggo culture as one of the vital points of the inquiry. All these conceptual themes summed up Sinamba sa Paraw Regatta in the eyes of Grupo del Oeste.