SPRINGFIELD, Mass. (WGGB) — The line-of-duty death of a Springfield Police officer Monday brings back memories of previous officers who also have either been injured or have lost their lives protecting their city.

The last time a local police officer died in the line of duty was in 1999.

On December 22, 1999, 52-year-old Holyoke Police Officer John DiNapoli, who was off duty, responded to a call to break up a fight. He was shot by Eddie Morales, while he sat in his unmarked cruiser at Hampshire and Walnut Streets.

Morales fled and was captured a few days later in Scranton, Penn. He is serving life in prison on a first degree murder conviction.

The last Springfield police officers killed in the line of duty were Alain Beauregard and Michael Schiavina on November 12,1985.

Both were shot during a traffic stop on Stebbins Street. 28-year-old Schiavina died that night, while 29-year-old Beauregard died a few days later.

The shooter, Eduardo Ortiz, killed himself the next day in a Plainfield Street hideout.

His brother, Juan Ortiz, was convicted of second degree murder and is serving life in prison.

On April 30, 2011, a Springfield police officer and a Massachusetts state trooper were shot by an escaped inmate.

Tamik Kirkland opened fire on the two from the trunk of a car that police say he was using to escape.

Each were shot once, but were wearing Kevlar vests. Police were pursing Kirkland after they say he shot two men inside a Springfield barber shop. One of them was killed.