The Waterloo was built in Bristol in 1815. Convicts were transported to New South Wales on the Waterloo in 1829, 1831, 1833, 1836 and 1838 and to Van Diemen's Land in 1835.
Convicts transported on the Waterloo in 1833 came from counties in England, Scotland and Wales - Lancaster, York, Middlesex, Stafford, Chester, Worcester, Surrey, London, Essex, Nottingham, Hertford, Sussex, Warwick, Kent, Leicester, Derby, Bristol, Worcester, Flint, Edinburgh and Glasgow,
The Guard consisted of 8 rank and file of 4th regiment., 2 women and 7 children under orders of Capt. Mondilhan of 54th and Lieut. Lackie of 39th regiment.
Surgeon John Stephenson
John Stephenson kept a Medical Journal from 17 February to 21 August 1833. He detailed in his journal the difficulties experienced before the Waterloo departed England......
The Waterloo arrived in Sheerness from Deptford on 3rd March and by the 10th March had received 214 convicts. One of those men was William Death aged 28 who was put on the sick list suffering from pneumonia and typhus on 6th March. He died on 10th March 1833.
After this unfortunate beginning the surgeon was hopeful that there would be no more sickness, however on the morning of the 12th March while preparing to get under weigh, the mother and wife of convict Robert Coney (age 28) were allowed on board to see him.....Whilst talking with them on deck, he was suddenly seized with vertigo, universal tremor, nausea and vomiting, and such a state of weakness that he was unable to support himself. He was taken below and in less than an hour had every symptom of malignant cholera. At first his symptoms, which included tremor, nausea and vomiting, were supposed to be the effect of 'mental affection' on seeing his wife, the surgeon was called to see him an hour afterwards. 'He became insensible and died about 2am on the 14th. 
Three days later they returned having lost all three anchors in a gale off Margate. They stayed until the 27th and then sailed to the Mother bank where a serious outbreak of cholera forced them to remain in quarantine until 8th April 1833. 
Illness On Board
John Stephenson was experienced in treating cholera as he had encountered similar conditions on the Katherine Stewart Forbes the previous year. The sick were removed to the Tremendous and the convicts joined them a few hours a day while the ship was thoroughly cleaned.
About 40 convicts were treated for cholera and several men died of the disease. Another convict William Death died of Pneumonia. Two of the men who died of cholera weighed heavily on the mind of the surgeon. They had been attendants on one of their mess mates who had been struck with the illness. Both contracted the disease and died almost immediately. There were no further outbreaks past the 9th April and the surgeon ordered the clothing and blankets of the dead to be destroyed. He was dismayed to later discover that 'the wretches had actually slept night after night under the blankets I had ordered to be destroyed'. 
The following deaths occurred.....
John Bilby died 6th March 1833
William Watts age 17, died 22 March 1833
Robert White age 29, convict died 19 March 1833
Samuel Gill age 22, convict, died 21 March 1833
George Harris, convict died 22 April 1833
Edward Evans died 19th March 1833
Thomas Emerson age 19 died 1 June 1833
Thomas Knowles died 21st March 1833
Thomas Monday died 21st March 1833
Other convicts, soldiers and passengers treated by the surgeon included:
John Getcliffe age 37, convict
Henry Trevillion age 20 convict
Jonathan Skipps, aged 17, Convict;
Thomas Stockton, aged 20, Convict;
Jonathan Bailey, aged 38, Convict;
Richard Yeadon, aged 17, Convict;
Jonathan Flinn, aged 16, Convict;
Robert Ney (Nay), aged 15, Convict;
Private Coleman, aged 23, [soldier of the] 21st Regiment;
Private Maher, aged 24, [soldier of the] 21st Regiment;
Daniel Conolly, [soldier of the] 21st Regiment; disease or hurt, gunshot wound. Died, 11 May 1833.
James Henry Fullerd, aged 23, Convict;
Private Turnbull, aged 20, [soldier] of the 21st Regiment;
Jonathan Richardson, aged 17, Convict;
Mrs Campbell, [age and quality not recorded]; disease or hurt, labour.
Private Coleman, [soldier] of the 21st Regiment;
Joseph Adulphus Clifford, aged 17, Convict;
Private Campbell, [soldier] of the 21st Regiment;
Richard Brooks, , Convict;
John Peeling, aged 21, Convict;
John Sutcliffe, Convict;
William Neville, aged 7, Soldier's Child; disease or hurt, disease of spine.
Mrs Neville, [age not recorded]; disease or hurt, labour. Put on sick list, 30 June 1833.
Jonathan Smith, Convict;
Thomas Wilson, Convict;
George Powell, aged 40, Convict;
Samuel Brooks, Convict;
George Hunter, Convict. 
Three weeks of bad weather after sailing made it impossible to keep the prisoners clean or dry and they were forced to remain below decks much of the time. Few convicts had changes of clothes. The end of April and all of May the weather was fine, June and July were very bad with gales, rain and hail. During the rest of the passage the prisoners mostly enjoyed good health although one more convict passed away.
The surgeon noted in his journal the death of one of the Guard, Private Daniel Conolly - Whilst sentry on the poop his musket went off by accident and the ball entered between the 6th and 5fth ribs on the right side and passed outwards to the top of the shoulder leaving a large hole and copious bleeding from both points. Despite such serious internal injuries he lived for another three hours.
The Waterloo arrived in Port Jackson on 3 August 1833 with 203 male prisoners. Information in the convict indents includes name, age, education, religion, marital status, family, native place, trade, when and where convicted, sentence, prior convictions and physical description. Additional information such as dates and place of death after arrival, pardons and colonial crimes are also occasionally included.
Many settled to a new way of life. They were granted tickets of leave or certificates of freedom and they married and raised families. There were others however who did not adapt and in desperation to escape unending toil and harsh punishments, they took to the bush. Among them were -
George Castle who absconded from the Newcastle hospital in 1836;
George Edwards absconded from an escort in 1841;
Richard Jones absconded from John Pike in 1834;
Robert Sheldon absconded from William Burnett in 1838.
None of these men however, achieved the notoriety and daring of Henry Elgar who in 1844 joined with several other desperadoes to steal a boat from Newcastle harbour and sail northward. They abandoned the boat north of Port Stephens and took to the bush but were eventually captured by the Mounted Police and sentenced to a penal colony for life.
Notes and Links
1). The Waterloo under Captain Henry Agar and surgeon Henry Kelsall was wrecked at Table Bay in 1842 while on the voyage from Sheerness to Tasmania.
2) John Stephenson was employed as Surgeon Superintendent on the convict ships Guildford in 1829, Eleanor in 1831, the Katherine Stewart Forbes in 1832 (VDL) the Waterloo in 1833. He lost his life in the wreck of the Neva in 1835.
3). National Archives... Reference: ADM 101/73/3 Description: Medical and surgical journal of His Majesty's hired ship the Waterloo for 17 February to 21 August 1833 by J Stephenson, Surgeon, during which time the said ship was employed in conveying convicts to New South Wales
4). Convict Ships bringing detachments of the 4th (King's Own) Regiment
Jane departed Cork 29 April 1831. Commander of the Guard Captain George Mason
Surry departed Portsmouth 17 July 1831. Commander of the Captain Waldron 38th regt.
Asia departed Cork 6 August 1831. Commander of the Guard Captain Richard Chetwode
Norfolk departed 15 October 1831. Commander of the Guard Lieut. David William Lardy 4th regt.
Captain Cook departed Dublin 5 November 1831. Commander of the Guard Lieut. Gibbons 49th regt.