22 December 1940
Italian bombers were again reported in the vicinity of Port Sudan. Three Gloster Gladiators Mk II of K Flight and two Hawker Hurricanes Mk I of No.1 (SAAF) Squadron took off to intercept them, without result. Pilot Officer Alan Tofield suffered a head injury when his aircraft hit an obstacle during takeoff at 08:55. His aircraft, Gloster Gladiator Mk II K 7974, is completely destroyed.
Gloster Gladiator K7974, then in service with No.601 (RAF) Squadron in 1938. The aircraft is destroyed on takeoff (Pilot Officer Philip J. Toefield) when it hit an obstacle at Port Sudan on December 22, 1940.
Following the failed attempt on 19 December, Flight Sergeant Keith took off in a Vickers Wellesley to drop supplies for Mission 101. Once again, the crew has difficulty locating the area (the drop is about 25 km away) but most of the supplies are recovered.
Finally, No.14 (RAF) Squadron learned of the award of the DFC, on this day, for Squadron Leader Deryck C. Stapleton.
« Acting Squadron Leader Deryck Cameron Stapleton, A.F.C. (37948), No. 14 Squadron. Squadron Leader Stapleton was the leader of two formations in a combined attack against a target in Eritrea. South of Massawa, they were intercepted by enemy fighters and an engine of one of our aircraft was put out of action. The pilot endeavoured to escape, but was followed by an enemy fighter and eventually forced to land in enemy territory. Squadron Leader Stapleton, having shaken off the fighters, ordered the remainder of the second formation to join up with him and successfully attacked his alternative target. He then returned to the coast to search for the missing aircraft, which was sighted and observed to crash on landing. Squadron Leader Stapleton landed alongside, and waited while the crew set fire to their papers. He then emplaned the crew in his own aircraft, and flew back to base with the rest of the formation, which had been circling overhead. Courageous leadership, skill and daring are characteristic of all this officer’s operations against the enemy. »
The description refers to the events of 26 November 1940.
 K Flight: Operations Record Book (Form 540 and Form 541). Kew : TNA, AIR 29/858; No.1 (SAAF) Squadron : War Diary. Kew : TNA, AIR/54/1.
 No.47 (RAF) Squadron : Operations Record Book (Form 540 and Form 541). Kiew: TNA, AIR 27/463.
 No.14 (RAF) Squadron : Operations Record Book (Form 540 and Form 541). Kiew: TNA, AIR 27/192.
 The London Gazette, 7 January 1941.