January 12, 2017 02:26 PM

The esteemed principal of a Missouri high school was led out of his office in handcuffs this week on statutory rape allegations that date back nearly 20 years, PEOPLE confirms.

Veteran educator Matthew Lindsey — honored in 2015 by the Greater Kansas City Missouri Principal’s Association as its “principal of the year” — was arrested Wednesday afternoon inside Winnetonka High School in Kansas City, Missouri.

He remains in custody at the Ray County Jail on $50,000 cash bond.

An affidavit obtained by PEOPLE claims Lindsey, a 48-year-old married father living in Oak Grove, Missouri, had sex with an underage female student approximately 20 times over an eight-month period, between October 1997 and May 1998. Authorities allege the relationship began when the student was 16 and Lindsey was approximately 29.

During that school year, Lindsey was the assistant principal, athletic director and boy’s basketball coach for the high school in Richmond, Missouri, where his alleged victim was a student. She graduated in 1999, according to court records.

The affidavit describes the girl as an underage cheerleader Lindsey had befriended on the school bus to out-of-town basketball games, when they would sit together.

The victim told investigators she was 16 when she first allegedly met Lindsey for sex at his former residence in Richmond and a hotel in Lafayette, Missouri, according to court records.

The affidavit claims Lindsey gave the girl gifts and cash over the course of their affair, which turned physical after Lindsey asked the victim if she did “deliveries” for the pizza place where she worked.

The victim told police Lindsey gave her money to buy a dress on her 17th birthday, the affidavit alleges. The victim also told detectives a friend knew of her alleged encounters with Lindsey, and the friend confirmed to police driving the victim to Lindsey’s home on several occasions.

According to the affidavit, the alleged victim came forward with her allegations in late October. The affidavit does not indicate what prompted the victim to report her alleged sexual relationship with Lindsey nearly two decades later. A Ray County prosecutor’s spokeswoman declined to address the gap between Lindsey’s alleged crimes and his arrest Wednesday.

“To me, it is important that kids are protected,” prosecutor Camille Johnston told the Kansas City Star. “So if this happened 20 years ago, it could possibly be happening now. I just want to make sure that our schools are safe, so that is why I went ahead and prosecuted it at this point.”

Neither Lindsey’s attorney nor his school district could be reached for comment Thursday.

He has been placed on administrative leave in light of his arrest and has yet to enter a plea to the two statutory rape charges against him.

In 2015, Lindsey accepted a four-year term as a board member of the National Association of Secondary School Principals. He has been Winnetonka High School’s principal for 10 years.

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