Gary Heather, 51, and Kirsty Horsted, 22, made silent calls and threatening comments to Sally Dixon.
The pair denied the crime and were due to stand trial but admitted harassment when they stood in the dock.
Earlier this year in a separate case Horsted, of Middle Park Way, Leigh Park, had previously admitted two counts of harassment.
During the earlier hearing, in which Heather was not involved, Portsmouth Magistrates’ Court heard how Horsted showed no remorse and even asked a probation officer: ‘Do you think I’ll get away with it?’
Graham Heath, prosecuting, said when asked why she was transphobic, Horsted said she ‘knew it would hurt and upset’.
Horsted harassed Ms Dixon between December 20 and 23 last year, and again while on bail between January 12 and 29 this year. Horsted sent three transphobic messages, with one saying: ‘You’re nothing but a man.’
Mr Heath said: ‘[Ms Dixon] said this did offend her as she identifies as transgender.
‘It’s clear that she did wish to cause this lady the grief that she did.’
The court heard Horsted also sent takeaway pizza to the victim’s home and threatened to damage property.
Mr Heath said: ‘Some incidents taken in isolation are relatively minor but because of them ongoing, in terms of telephone calls, threats to damage property, sending pizza round that was not ordered by her and such like, this over the period of time, caused great concern.’
Horsted was arrested and bailed but continued to contact Ms Dixon, a former friend. On January 22 Horsted posted ‘unpleasant’ messages on Ms Dixon’s business Facebook page. Mr Heath said the victim has been left feeling ‘anxious’ and said the stress made her ill.
Rhys Evans, defending, admitted Horsted’s actions were unpleasant.
Magistrate Peter Mellor sentenced her to three weeks in prison suspended for 12 months with 12 months of supervision and 20 days of rehabilitation activities. A restraining order banned her from contacting Sally Dixon or her sister Sheena Dixon for a year. She was told to pay a £60 victim surcharge and £85 prosecution costs.
The first harassment charge was aggravated by her transphobic comments.
At the second case on April 4, involving Horsted and Heather, they both pleaded guilty to harassment between February 4 and February 8.
Heather received a community order with a six-week electronic tag. A restraining order bans him from contacting the Dixon sisters. He must pay a £60 victim surcharge and £185 costs. Horsted was handed a 10-week sentence suspended for 12 months. She must pay the same as Heather.