He was educated at Cloyne Diocesan School, Mallow, and at Trinity College Dublin, where in 1863 he obtained Mathematical Honours in the Hilary term examinations.

He was accused of deliberately allowing the trial to take place in a racist and hostile town that would be expected to acquit the murderers due to local influence, and thereby of dereliction of the Attorney General's duty.

[1][2][3] He became the fourth Prime Minister of the Cape Colony in 1884, after the growing Afrikaner Bond Party compelled the government of Premier Thomas Charles Scanlen to retire.

He was appointed to form a government by the powerful Afrikaner Bond, but held office for only two turbulent and strife-torn years, in what subsequently became known as the "Warming-pan" Ministry.

The issue placed Upington in a near impossible position as he owed his parliamentary support to the Afrikaner Bond which was strongly sympathetic of the Boer states, while the British Imperial authorities demanded his action.

He was accused of propounding Parnellite principles and denounced by British politicians in Cape Town as a “Fenian” whose "offence is rank", and who "has been fraternising with Mynheer Van Dunk instead of sticking with John Bull".

Regarding internal development of the country, Upington attempted to continue the highly successful locally oriented economic policies of his predecessors Molteno and Scanlen.

Some of his policies (such as reintroducing the infamous Contagious Diseases Acts) also brought him into conflict with the powerful liberal lobby, represented by Saul Solomon, which saw them as discriminatory against the black citizens and voters of the Cape.

After coming under a fresh wave of attack over his Basutoland policy, he resigned "due to ill-health" in 1886, and handed over to his pro-imperialist ally John Gordon Sprigg.

Though the two men opposed each other on nearly every point, they had very similar rapid-fire and flowery debating styles, that made their frequent arguments very entertaining to observe in parliament.