From Pensapedia, the Pensacola encyclopedia
- May 31 – Nicole Pfister is booked for allegedly forging Gulf Power documents related to former Front Porch Pensacola community liaison Thelma Manley.
- May 29 – A fire erupts at the Gulf Power Crist Plant, injuring four contractors.
- May 29 – The Emerald Coast Utilities Authority unanimously approves five contracts, in total worth more than $144 million, related to moving the Main Street Wastewater Treatment Plant.
- May 28 – Thelma Manley is arrested for aggravated white-collar crime for allegedly stealing nearly $150,000 from Front Porch Pensacola while serving as its community liaison.
- May 28 – The Gulf Coast Center for Innovation and Entrepreneurship is dedicated by Pensacola Junior College and the Pensacola Bay Area Chamber of Commerce at the PJC Downtown Center.
- May 23 – Celebrate Pensacola begins its 450-day celebration with a kick-off party at the Escambia County Courthouse.
- May 22 – The Town of Century receives a $1.4 million loan to expand its water system.
- May 21 – A groundbreaking ceremony is held for the new Tryon Branch Library on Langley Avenue.
- May 20 – Pensacola Mayor John Fogg announces he will not seek reelection, citing a desire to participate in the "strong mayor" debate without a perceived conflict of interest.
- May 15 – Escambia County Superintendent Jim Paul releases a list of 31 cost-saving recommendations, including the closure of Carver-Century K-8 School.
- May 13 – Roads, Inc. president Cody Rawson and his wife host a fundraiser for Escambia County Commissioner Mike Whitehead.
- May 13 – The City of Pensacola Planning Board unanimously approves new regulations regarding heritage trees.
- May 12 – UWF President John Cavanaugh announces he will leave the university to become chancellor of the Pennsylvanis System of Higher Education, effective July 1.
- May 9 – Grace Resendez McCaffery is selected to fill the Community Maritime Park Associates seat vacated by Susan Story.
- May 9 – The eastern 3-mile stretch of J. Earle Bowden Way, which connects Navarre Beach to Opal Beach and was destroyed in Hurricane Ivan, reopens.
- May 8 – The Pensacola City Council votes 6-3 to hire Rusty Wells as the new city attorney, foregoing the agreed upon candidate ranking process.
- May 8 – Kimberly Mary Cannon is charged for the 1995 murder of her husband, Daren Kelley, after a human leg bone was discovered on the Munson property where they resided.
- May 7 – The Publix supermarket opens in the Sea Shell Collections shopping center in Gulf Breeze.
- May 5 – U.S. District Attorney Greg Miller announces his resignation, effective the end of June, and will open a Tallahassee branch of law firm Beggs & Lane.
- May 3 – Criminal neglect charges against Erin Markes are dropped, after a three-month investigation into her son Jaden's health.
- May 1 – Susan Story resigns from the Community Maritime Park Associates Board of Trustees.