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- June 30 – The UWF Board of Trustees unanimously approves an annual contract worth $238,000 for interim president Judy Bense.
- June 27 – Capt. William P. Reavey, Jr. is installed as commanding officer of Pensacola Naval Air Station, replacing Capt. Peter S. Frano.
- June 26 – Baptist Health Care announces a $330 million expansion that, if approved, will include the purchase of West Florida Hospital on North Davis Highway.
- June 25 – Florida Supreme Court Justice Kenneth Bell tenders his resignation, effective October 1.
- June 24 – The Davis Highway Barnhill's buffet restaurant owned by Charlie Barnhill closes, putting about 65 employees out of work.
- June 24 – Conceding that U.S. District Court lacked the proper jurisdiction, Judge Lacey Collier lifts his earlier injunction that would have allowed sprinter Justin Gatlin to participate in the 2008 Olympic trials.
- June 23 – The ECHL terminates the Pensacola Ice Pilots' league franchise after team owner Mario Forgione says he will not field a team for the 2008-09 season.
- June 20 – Non-profit research institute TaxWatch unveils a 37-page report critical of the Escambia County budget.
- June 19 – The Escambia County Commission votes unanimously, with no discussion, to settle a lawsuit filed by Roads, Inc. over the revocation of a stormwater permit at the company's controversial Cantonment catfish pond.
- June 18 – Northrop Grumman KC-45 plant: The Government Accountability Office recommends that the Air Force reopen bids for a $35 billion refueling tanker contract.
- June 17 – The UWF Board of Trustees unanimously approves Dr. Judy Bense to replace John Cavanaugh as University of West Florida president.
- June 17 – Pensacola City Manager Tom Bonfield tenders his resignation, effective August 8, having accepted a similar position in Durham, NC.
- June 16 – Restoration Full Gospel Baptist Church pastor Leon Rankins III is sentenced to five years in state prison for molesting a teenaged parishioner.
- June 15 – A fire guts the Oar House restaurant on Bayou Chico.
- June 13 – Randy Bell is crowned De Luna LIX by Fiesta of Five Flags.
- June 13 ‐ Solutia announces a $182 million deal with three Chinese companies to manufacture vydyne, a heat-resistant nylon-based plastic, at its Pensacola plant.
- June 12 – The Pensacola Lightshouse reopens to visitors with a ceremony attended by Governor Charlie Crist.
- June 10 – Angela Leavitt, suspected of having a sexual relationship with a 16-year-old boy, is arrested at Pensacola Regional Airport with her two children.
- June 9 – National grocery chain Publix announces it will buy all four Albertsons locations in the Pensacola area.
- June 9 – A $15 million cleanup plan is announced for the "Mount Dioxin" Superfund site at the former Escambia Treating Company.
- June 7 – The inaugural Palafox Market is held in Martin Luther King Plaza.
- June 5 – Facing criticism for attending a political fundraiser by Roads, Inc. owner Cody Rawson, who had sued the county, Mike Whitehead steps down as chairman of the Escambia County Commission.
- June 5 – The Pensacola Opera dedicates their renovated headquarters, dubbed the Donald H. Partington Center.
- June 3 – 28-year-old Angela Leavitt goes missing, along with her two children and a 16-year-old boy with whom she was suspected of having a sexual relationship.
- June 3 – Pensacola City Manager Tom Bonfield is offered the city manager position for Durham, NC.
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- 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.
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