[6] Cypress Bay's Boys' varsity soccer team has won the FHSAA Class 5A State Championship five of the last seven years.

[11] Kimberly Blum, Michael Orlando, Isabella Chiappini, Alex Lann from Cypress Bay was awarded first place in the Broadcast News - High School competition at the SkillsUSA National Leadership and Skills Conference in Atlanta, Georgia.

This did not occur again until the class of 2012, when the graduation ceremony took place at the freshly completed Marlins Park and Vice President Joe Biden delivered the keynote address.

[20][21][22][23][24] In 2015, rapper Flo Rida collaborated with then-school principal Charles Neely to create a spin-off rap video based upon his song G.D.F.R (Goin' Down for Real).

The video features the principal rapping with several students and staff, and was a congratulatory message to the graduating class.

[25] In early 2019, construction began on a new building at Cypress Bay High School[26] to alleviate the overcrowding issue.