Kerala has a long history with the outside world since ancient times. It had trade contact with King Solomon referred to in the Old Testament. Later, it enjoyed its hay days with the Romans. Many of its ports like Musri’s and Kollam were famous for their spice trade pepper, teak wood, sandalwood, and tortoise shells were exported to European countries during the classical period. With the advent of the Christian Era, it was one of the places visited by St Thomas in 52 A.D, followed by the migration of Syrians and they too settled inside the state. The Syrian Christians have been practicing Christianity long before the advent of the Portuguese. The monument that stands testament to that tradition is Thevalakkara Marthamarium Church. Later in the 16th century Portuguese domination came into being. A grandiose epitome of the legacy of the Portuguese in Kerala is the Kovilthottam St Andrews Church, which is one of the earliest churches in the Kollam diocese. Kovilthottam Church is a fledgling parish with 1000 families which is threatened by the approach of the sea and mining of rare earth minerals can trace its origins to the early Christians of Kerala, whose preservation is a matter of protection of its age-old traditions, customs, and heritage. This article is trying to do a one to one study of the two distinct historical monuments, their history and how they are connected both historically and culturally. The method employed in this study is that of descriptive in nature. The research done for this article included field visit, architectural documentation, interviews, going through previous scholarly works, use of original sources. By comparing these monuments we are contrasting the existence of two distinct religious sects and how they interacted with history during their time of existence.