Pada 11 September 1508, Raja Portugal, Raja Manuel telah mengutuskan Lopez de Squire dengan rombongan telah tiba di Melaka. Awalnya, utusan ini disambut baik oleh Sultan Melaka, namun akhirnya 18 orang Portugis telah ditangkap dan dipenjarakan di Melaka. Rombongan Portugis telah meninggalkan Melaka setelah permohonan untuk melepaskan tawanan ditolak. Pada tahun 1509, Portugis mula menyerang Melaka namun tidak berjaya menumpaskan Melaka. Kemudian pada 24 Julai 1511 sekali lagi Portugis datang menyerang Melaka yang akhirnya Melaka tumpas pada 24 Ogos 1511, Melaka jatuh ke tangan Portugis manakala Sultan Mahmud Syah dan puteranya, Sultan Ahmad berundur ke Johor. Maka berakhirlah Kesultanan Melayu Melaka yang bertapak di Kota Melaka selama 111 tahun.

On September 11, 1508, King Manuel of Portugal dispatched Lopez de Squire and his entourage to Malacca. This ambassador was first accepted by the Sultan of Malacca, but 18 Portuguese were later caught and imprisoned in Malacca. After the plea to liberate the hostages was denied, the Portuguese team left Malacca. The Portuguese launched an attack on Malacca in 1509, but they were unsuccessful. The Portuguese then came to attack Melaka again on July 24, 1511, and it ultimately fell into their hands on August 24, 1511, while Sultan Mahmud Syah and his son, Sultan Ahmad, escaped to Johor. Thus, the Malacca Malay Sultanate, which had been based in Malacca for 111 years, came to an end.