The two cases happened in the early hours Cambridge Road and Burnaby Road.
Winchester Prison Slammed In New Report
A new report has criticised Winchester prison for having problems with drugs, overcrowding and violence.
In one case, two severely disabled inmates were found crammed into a Victorian cell designed for one for nearly 24 hours a day during an inspection.
The two older inmates at HMP Winchester had not showered for months and relied on other prisoners to take them their meals, HM Inspectorate of Prisons (HMIP) found.
Elsewhere, one third of the 680 prisoners told inspectors illegal drugs were "easily available", while one in 10 developed a drug habit within the jail walls.
The category B prison, partly built in the 19th century, has deteriorated sharply and is now of serious concern, Chief Inspector of Prisons Nick Hardwick said.
"Until shortly before the inspection, HMP Winchester was neglected and drifting,'' Mr Hardwick said.
"There had been pockets of good practice and, although many staff did their best, their efforts were often haphazard, inconsistent and badly coordinated.''
In a damning report, the inspectorate said that more than half of prisoners had felt unsafe at some time, while there was insufficient action to tackle violence.
Inspectors witnessed "foul abuse" towards vulnerable prisoners in the exercise yard and processes for locating prisoners on to the vulnerable wing were unclear.
Almost four out of five vulnerable prisoners felt unsafe at some time, while "inappropriate sexual images" of naked women were found on the vulnerable prisoner wing.
The day-to-day experience of many prisoners was found to be poor, with insufficient activity places, the Inspectorate found.
Staff were unaware that the two older and disabled prisoners could not use the shower on their landing as it was not adapted accordingly.
The men had a small window in their cell that was painted over so they had to choose between keeping out the cold or shutting out the light, the report added.
Resettlement work - preparing prisoners for release in a bid to cut reoffending - was "weak'', the report said.
The Inspectorate also found that resources were "very stretched'' with problems made worse by a lack of a "stable" leadership.
Mr Hardwick said a new governor was appointed shortly before the inspection.
He said: "The new leadership was aware of many of the problems and we saw early signs of a determined effort to tackle them.
"But the prison is just at the start of the process of putting things right again, and it will be a long, hard task to do so."
The prison is divided into two parts with a larger Victorian site and a smaller annexe, known as West Hill, which was built in the 1960s.
National Offender Management Service chief executive Michael Spurr said: "I accept that performance at Winchester has fallen short of the standards expected.
"As the chief inspector acknowledges, the new governor has begun to tackle the deficiencies and I am confident that these will be properly addressed and rectified.
"In particular, concerns about levels of violence and first night procedures are being robustly tackled - and we are urgently putting enhanced measures in place to address the supply and circulation of illicit drugs."
Lewis Hine - who has a brain tumour - posted an inspirational film about his life, on his 16th birthday last week.
One of the men's targets was Ernest Jones in Portsmouth, taking £57,000 worth of watches.
Detectives Searching For Dash Cam Footage Around Gilpin Close.
Recently Played Tracks
Now playing: Non-stop hit music
Deposit £10 to get a £40 Welcome Bonus - That's £50 to play bingo, slots and more!*
Over 50 tracks to make you feel-good. New album out now...
Find your local four day weather report here.
What's happening on the roads where you are?
Make Heart the soundtrack to your day and you could be a winner with great prizes up for grabs throughout the day.
Find out more about some of the companies advertising on Heart.
Get some great ideas on how to advertise your business on radio, online and on mobile.