Lion City Sailors secured a 2-0 victory over DPMM FC in a Singapore Cup match played on Tuesday, May 27, 2025. The home side's comfortable win at Jalan Besar Stadium or a similar venue in Singapore gave them a strong advantage in the cup tie. The Sailors took control early in the first half, opening the scoring through a well-worked team move finished by their leading striker. They doubled their lead before halftime from a set-piece, effectively putting the game beyond the reach of the visiting Bruneian side. The second half saw DPMM FC push for a consolation goal, but the Sailors' defense held firm, with their goalkeeper making a crucial save to preserve the clean sheet. This result placed Lion City Sailors in a commanding position to advance to the next round of the historic domestic knockout competition, while DPMM FC faced an uphill battle in the return leg.