A bust-length portrait of the Maharajah Dalip Singh, depicted in profile to the right. Signed and dated at lower right.

Winterhalter was the premier portraitist in the mid-nineteenth century at many of the major European courts, working for those of London, Paris, Belgium, Berlin, Vienna, Madrid and St Petersburg, amongst others. He painted over 100 portraits for Queen Victoria and her extended family; the Queen esteemed him especially for his ability to capture a likeness, and the elegance, romance and naturalism of his works. Winterhalter painted a full-length portrait in oils of the Maharajah for Queen Victoria at Buckingham Palace in July 1854 (see RCIN 403843).

Dalip Singh was the last Maharaja of the Sikh Empire. He was exiled in 1849 at the age of thirteen, following the British annexation of the Punjab in the Second Anglo-Sikh War. Dalip Singh arrived in London in 1854 and was received by Queen Victoria at Buckingham Palace on 1 July 1854. After their first meeting, the Queen described the young Maharaja in her journal as "16 & extremely handsome... [he] has a pretty, graceful & dignified manner. He was beautifully dressed & covered with diamonds". Dalip Singh was invited to stay with the Royal Family at Osborne that summer, where he continued to make a favourable impression on the Queen, who was later to become Godmother to the Maharaja's first child. He then stayed at Windsor Castle from 13 to 15 November 1854 after a visit to Edinburgh.

In 1864, Duleep Singh married Bamba Müller in Cairo and established his family home at Elveden Hall in Suffolk; he married again after Bamba's death in 1887 and had eight children in total. He later became disaffected and embittered with the British, reverting to his former faith, Sikhism, and launching a renewed claim on the Punjab. Although he had plans to return to India he died in France in 1893, having latterly achieved a reconciliation with Queen Victoria.