Robert Ellis, 50, met one of the 15-year-old victims online in April 2015.
He invited him to football matches, claimed to have talent spotted goalkeepers and offered to coach the teenager, who was from Lincolnshire.
Ellis, a civil servant of Church End, Harlow, arranged to meet him in a park in July 2015 where they played football and later went for a meal.
The boy’s mother reported Ellis to local police after finding out and banned her son from contacting him again.
However they resumed contact in December 2015 and arranged to meet. This was reported to police and Ellis was arrested in January 2016, before the meeting could take place
During the course of their enquiries, officers spoke to another young man, who said he had been in a sexual relationship with Ellis when he was 15 after they met online.
The victim told how they had twice engaged in sexual activity, once after Ellis had taken him to Chessington World of Adventures and the second time after he had taken him out for dinner.
During the police investigation, it was also found Ellis had been banned by the Football Association from taking part in any FA-football related activity involving under 18s, since December 2013. However, he continued to take part in informal football sessions in Harlow that were not covered by this ban.
Whilst on bail, Ellis met a 14-year-old boy and engaged in sexual touching with him
He was further arrested and remanded.
Ellis denied one charge of meeting a boy aged under 16 following grooming, six counts of engaging in sexual activity with a boy aged under 15 and three counts of sexual touching. He stood trial at Chelmsford Crown Court, where he was found guilty of all charges on February 28.
He was sentenced today, Friday April 7, to nine years and made subject of a sexual harm prevention order and will be added to the sex offenders register for life.
Speaking after the hearing, investigating officer Detective Sergeant Clayton Ford, of Essex Police’s Online Investigation Team, said: “This is a worrying grooming case where Ellis used his love of football and the suggestion of gifts or trips to various places to try and get a teenage victim into a situation where he could carry out sexual acts with him.
“Thankfully the victim’s family were able to recognise the risk from the messages exchanged and report the situation to police.
“Where Ellis was able to get unsupervised access to the other teenagers in this case, he went on to commit serious sexual offences.
“This case highlights the dangers of manipulative individuals operating on the internet looking to identify and exploit vulnerability or a common interest that will give them the opportunity to meet children for their own sexual gratification.
“I am grateful to the victims, whose courage and assistance has been essential in Ellis’s prosecution and possibly preventing further victims coming to harm.
“I would urge all children, and their parents or guardians, to have a look at the www.thinkuknow.co.ukwebsite and to be vigilant about the motives of people they do not know who approach them online.”