TOPIC:

Robert James Bennett enlisted in the Imperial Yeomanry on 23 March 1900 at 68 Victoria Street, London. His attestation papers record him as 20 years old, a Clerk by trade, born in the parish of Hackney, London.

On enlistment, Bob was described as 5 feet 9 inches tall, weighing 10 stone lbs, with a chest measurement of 33–37 inches, medium complexion, blue eyes, and dark brown hair. He was medically certified fit for service and appointed to the 72nd (Rough Riders) Company, 20th Battalion Imperial Yeomanry.

Anglo Boer War
Bennett embarked for South Africa on 14 April 1900, his service record shows he remained in South Africa until 27 May 1901, when he was discharged locally due to wounds received in action at Cypherfontein.

Imperial Yeomanry & the Imperial Light Horse
By early 1901, the Imperial Light Horse—once celebrated as the dashing Uitlander Regiment that had smashed Kruger’s invaders at Elandslaagte and held the line at Wagon Hill—was a very different unit. With the major Boer invasions seemingly defeated, many of the original volunteers had departed, leaving Woolls‑Sampson in command of two squadrons numbering about 200 men. Yet half of these were inexperienced recruits, while many of the remainder were disillusioned veterans, eager for long‑promised leave.

British High Command, already uneasy about Woolls‑Sampson’s impetuous leadership, sought to steady the regiment by attaching professional officers such as Major C.J. Briggs and reinforcing it with detachments from the Imperial Yeomanry. It was under this arrangement that Private R.J. Bennett, though formally of the Yeomanry’s 72nd (Rough Riders) Company, found himself serving within B Squadron of the ILH during Major‑General Babington’s pursuit of De la Rey in January 1901.

The Action at Cypherfontein, 5 January 1901
As 1900 ended, Boer commandos under De la Rey, Kemp, and Beyers intensified guerrilla operations. On 13 December 1900, they attacked General Clements’ camp at Nooitgedacht, inflicting heavy losses. In the aftermath, De la Rey and Kemp moved south towards Ventersdorp and Lichtenburg, pursued by General French, before doubling back north. Their movements brought them into contact with Major-General Babington’s column, operating west of Krugersdorp.

On 5 January 1901, Babington advanced with a force of 1,600 men, including squadrons of the Imperial Light Horse (ILH), to which Bennett was attached. Colonel Woolls-Sampson, commanding two squadrons of ILH, pressed forward rashly without adequate reconnaissance.

At Cypherfontein farm, De la Rey had positioned 700–800 Boers concealed in long grass. As Woolls-Sampson’s B Squadron advanced at a fast trot, they were ambushed at close range (50–100 yards).

The sudden fusillade devastated B Squadron. Horses panicked, men took cover behind dead mounts, and casualties mounted rapidly. Despite the chaos, survivors returned fire steadily. After ten minutes of intense fighting, Woolls-Sampson ordered a retreat. Casualties were severe: 18 killed and 32 wounded, overwhelmingly from B Squadron.

Bob was among the wounded, struck in the right shoulder, left arm, and jaw. In a letter to his mother dated 8 January 1901, he wrote with stoic understatement:

Shaun – I think the note outclasses the medal. As a Clerk in late Victorian times one would expect his writing to be copperplate or approaching, but with an injured right shoulder and left arm we see the result. In fact with an injured jaw as well communication was probably a major issue all round. Hopefully he fully recovered and was able to return to Clerking.

Hi David,

I couldn’t agree more—the letter was what first drew me to the lot, and the handwriting speaks volumes on several levels.

Setting aside his physical injuries, it’s remarkable that he wrote it just three days after enduring such a devastating firefight. I’m no expert, but it seems the handwriting falters once he moves past “Dear Mother” and begins to recount—almost re-live—the losses of that day. Then, as he closes with “Love to all, Bob,” the script steadies again. To me, it reflects the raw interplay of physical strain and emotional trauma.

Adding to the poignancy, I hadn’t shared this before: his mother had written to him, only to have her letter returned with the stark word “Killed” scrawled across it. I can only hope the shock did not cause her unbearable distress.



After the War
The trail of Robert “Bob” James Bennett grows faint, apart from the record that he later served as a Sergeant in the RASC during the First World War. Whether he went overseas or contributed to the war effort from England remains unclear. Attached is a copy of his WW1 file.

Picture courtesy of Noonan's

DSO GV;
MBE, 2nd type, civil;
QSA (5) Cape Colony, Orange Free State, Transvaal, South Africa 1901, South Africa 1902 (Lieut: A. K. Digby, Imp: Yeo:) officially re-engraved naming, the two date clasps contemporary tailor’s copies;
1914 Star, with copy clasp (Lieut. A. K. Digby, R.F.A.);
British War and Victory Medals, with MID (Major A. K. Digby.);
Defence and War Medals

DSO London Gazette 8 May 1915: ‘For conspicuous ability and gallantry during the campaign. He has been at the observing station on almost every occasion when his battalion was in action, and by his coolness and resource greatly contributed to the success attained. He was severely wounded at Neuve Chapelle on 10 March 1915.’

MBE London Gazette 1 January 1961: ‘Honorary Secretary, Lincolnshire Branch, Soldiers’, Sailors’ and Airmen’s Families Association.’

Arthur Kenelm Digby was born in 1879, son of Sir Kenelm Edward Digby, G.C.B, and the Hon. Caroline, daughter of the Rt. Hon. Edward Strutt, 1st Baron Belper. He was educated at Harrow and Corpus Christie College, Oxford (B.A. 1903). He entered the Royal Artillery on 25 April 1902, from the Imperial Yeomanry, becoming Lieutenant, 24 May 1905; Captain, 30 October 1914, and Major, 13 March 1916. He was Acting Lieutenant-Colonel R.A. from 3 January 1919. He served in the South African War 1901-02, with the Imperial Yeomanry; took part in the operations in the Transvaal, Maarch to May 1902; in the Orange River Colony, April 1901 to 31 May 1902; also in Cape Colony, April to May 1901 (Queen’s Medal with 3 clasps). In 1911 Major Digby married Violet, daughter of Sherbrooke Keatinge, late Indian State Railways. He served during the European War 1914-19, was twice wounded, mentioned in despatches (LG 22 June 1915), and awarded the DSO.

Lieutenant-Colonel Digby served in the Second World War between 1939 and 1941. He held the office of Deputy Lieutenant of Lincolnshire in 1961, and died at Cleethorpes, Lincolnshire, on 7 October 1966.