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.