The Philippine school system is considered as one of the largest in the world with 41,989 public elementary and secondary schools and 7,790 private schools under the supervision and regulation of the Department of Education [DepEd Fact Sheet, 2005]. On top of this statistics are 40 duly-registered educational institutions called the Philippine Schools Overseas, which operate in nine countries such as Bahrain, China, Greece, Kuwait, Libya, Oman, Qatar, Kingdom of Saudi Arabia, and United Arab Emirates. This paper presents the context and background of the proliferation of Philippine schools, specifically in the Kingdom of Saudi Arabia. To set the limits of the scope, this paper focuses on the strengths and weaknesses of community schools and privately-owned schools. Finally, the paper offers some vital measures relative to the supervision, standards of and support for Philippine Schools Overseas.