A disgraced headteacher has been ordered to pay compensation to an Ofsted inspector after sending him disturbing messages.

Gregory Hill, 49, pleaded guilty to three charges over messages targeting and hounding the inspector and two other senior education leaders in Norfolk. 

The offences occurred at a time when the former head of Howard Junior School in King's Lynn was facing allegations that he had become obsessed with a 21-year-old trainee teacher after she spurned his romantic advances.

Gregory Hill hounded Ofsted inspector who assessed his former Howard Junior School in King's Lynn following his arrestGregory Hill hounded Ofsted inspector who assessed his former Howard Junior School in King's Lynn following his arrest (Image: Chris Bishop)

He was jailed for 20 weeks in August after being found guilty of harassment and making unwanted advances.

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The latest charges related to him persistently sending or posting messages that caused annoyance, inconvenience and anxiety between December 2023 and February 2024.

They relate to online messages about Daniel Lambert, a lead inspector for Ofsted who carried out an emergency inspection of Howard Junior following the former headteacher’s arrest in March 2023.

He also persistently sent messages to Paul Shanks, chief executive of Eastern Multi-Academy Trust - which took over Howard Junior last December - and Phil Bugg, vice principal of King’s Lynn Academy.

Former headteacher Greg Hill during his arrest in March 2023Former headteacher Greg Hill during his arrest in March 2023 (Image: Norfolk Constabulary)

Hill, from Fakenham, was sentenced at Norwich Magistrates’ Court to four weeks in prison to run concurrent with his existing sentence and was ordered to pay £500 in compensation to each of the three people he sent messages to. 

Following the emergency Ofsted inspection Howard Junior was rated inadequate with Mr Lambert identifying “serious failings” which had gone “unchallenged for too long”.

READ MORE: School head Gregory Hill said he imagined teacher in bikini

During his harassment trial he was found to have hounded probationary teacher Chloe Regester over an 11-month period, bombarding her with dozens of social media messages declaring his love for her. 

Hannah Gidman, who alleges she was also subjected to inappropriate behaviour by Gregory HillHannah Gidman, who alleges she was also subjected to inappropriate behaviour by Gregory Hill (Image: BBC)

Five further women have since come forward with allegations of inappropriate behaviour.

All alleged Hill would frequently comment on their looks but said they did not make complaints at the time as they were worried it could threaten their jobs.

Hannah Gidman, 26, who worked at the school in 2019, told the BBC he would make "sexualising comments" towards her including telling her he could imagine her in a bikini, which she said made her feel "icky" and "uncomfortable".