In June 1940, 33 Squadron was based at Mersa Matruh, Egypt, commanded by Squadron Leader D. V. Johnson and equipped with 21 Gladiators (mainly Mk.IIs) (on 11 June) and six Gloster Gauntlets Mk.IIs kept in reserve. It had 22 pilots in three flights:
‘A’ Flight included Flight Sergeant Leonard Cottingham, Sergeant Roy Leslie Green, Flying Officer Monk, Pilot Officer Eric Woods, Pilot Officer Brown, Pilot Officer Preston, Pilot Officer Perry St. Quintin and Flight Lieutenant G. E. Hawkins.
‘B’ Flight included Flying Officer Ernest Dean, Sergeant Shaw, Pilot Officer Vernon Woodward, Sergeant Craig, Flying Officer Couchman, Flying Officer John Littler and Pilot Officer Alfred Costello.
‘C’ Flight included Flight Lieutenant Bolingbrooke, Sergeant William Vale, Pilot Officier E. K. Leveille, Flight Sergeant Harry Goodchild, Flying Officier Henry Starrett and Pilot Officier Boulton.

14 June saw the first combats between opposing RAF and Regia Aeronautica fighters over North Africa. This was caused because the 11th Hussars (Prince Albert’s Own), joined by elements of 4th Armoured Brigade and 1st Battalion, King’s Royal Rifle Corps, assaulted Fort Capuzzo and Fort Maddalena (the two most important Italian frontier posts). The offensive was supported by attacks by Blenheims from 45, 55, 113 and 211 Squadrons. To protect both bombers and ground forces, 33 Squadron flew offensive sweeps as far as Bardia, meeting the Regia Aeronautica two times in the morning and Craig took part in the second engagement.
At 10:00, after refuelling the Gladiators, Dean (Gladiator L9046) and Woodward (Gladiator N5783) were off again, followed a few minutes later by Sergeant Craig (Gladiator N5768). Near Fort Capuzzo they intercepted two Caproni Ca.310Bs escorted by CR.32s. Dean shot down one of the CR.32s while Woodward and Craig jointly attacked one Caproni, setting one of the engines on fire. The Italian bomber crash-landed among British tanks near Fort Capuzzo. Woodward also attacked and claimed a second CR.32 (this claim is unconfirmed and no more Italian losses has been possible to verify) before retuning to base with a single bullet hole in one of the wings. Dean later told:

“Soon after being promoted to Flying Officer, I was posted to No 33 Squadron at Mersa Matruh. I had a good flight with Verne Woodward, Peter Wickham and Sergeant Craig. It wasn’t long after Italy declared war that we were moved to Sidi Barrani. We had no warning system at all of aircraft movement by the enemy, and only very sketchy and vague locations of both ours and their positions from the Army. We carried out the old traditions of patrolling along and over the border in the beginning in “vics” and pairs. Later, we flew bigger sweeps with more aircraft. The combat of 14 June near Fort Capuzzo was our very first encounter with the enemy. An inoffensive-looking light bomber was seen, and I detached Woodward and Sergeant Craig to attack, whilst I stayed aloft to cover. Within a short spell, I saw six aircraft in line astern heading from the west. I recognised them as CR 32s. I remember being quite calm, and wondering what the heck to do. I flew towards them, keeping them well to my right – with the thought of getting behind them (and shooting them down one by one – silly boy!).
Before I got close enough to them, they split in all directions and formed a ring around me – the sitting duck! I remembered somewhere about flying extraordinarily badly to present a very bad target. I throttled back, yawed and waffled up and down and around, and could hear the thump of their half-inch cannon at each pass, and as each came into my sights having a rapid squirt at them. This seemed to go on for ages, and eventually one of them dropped away and suddenly the remainder disappeared, and I was thankfully alone in the sky and flew back.
I heard upon my return to base that one CR 32 had been destroyed, apparently by me, whilst Woodward and Craig had shared the bomber. I did hear later that the pilot of the CR 32 had been struck by a single bullet through the heart.”

Craig later followed the Squadron to Greece but nothing more is know of his career.

Craig ended the war with 1 shared biplane victory, this one being claimed while flying Gloster Gladiators.

Claims:

Kill no.	Date	Time	Number	Type	Result	Plane type	Serial no.	Locality	Unit
	1940
	14/06/40	½	10:25-11:40	Ca.310 (a)	Shared destroyed	Gladiator II	N5768	near Fort Cappuzzo	33 Squadron

Biplane victories: 1 shared destroyed.
TOTAL: 1 shared destroyed.
(a) Ca310 of 159^a Squadriglia, 12^o Gruppo flown by Sergente Maggiore Stefano Garrisi, crash-landed. Garrisi and 1^o Aviere Alfio Ubaldi parachuted while gunner Aviere Scelto Giuseppe Pascali jumped too low and was killed.

Sources:
2^o Stormo - Note storiche dal 1925 al 1975 - Gino Strada, 1975 USSMA, Rome, kindly provided by Ludovico Slongo
50^o Stormo d'Assalto - Nino Arena, 1979 STEM Mucchi, Modena kindly provided by Stefano Lazzaro
Aces High - Christopher Shores and Clive Williams, 1994 Grub Street, London, ISBN 1-898697-00-0
Aces High Volume 2 - Christopher Shores, 1999 Grub Street, London, ISBN 1-902304-03-9
Adriano Visconti Asso di Guerra - Giuseppe Pesce and Giovanni Massimello, 1997 Albertelli Edizioni Speciali, Parma, ISBN 88-85909-80-9, kindly provided by Ludovico Slongo
Gloster Gladiator - Alex Crawford, 2002 Mushroom Model Publications, ISBN 83-916327-0-9
Gloster Gladiator Aces - Andrew Thomas, 2002 Osprey Publishing, London, ISBN 1-84176-289-X
Gloster Gladiator Home Page - Alexander Crawford.
Fighters over the Desert - Christopher Shores and Hans Ring, 1969 Neville Spearman Limited, London
Il Fiat CR 32 poesia del volo - Nicola Malizia, 1981 Edizioni dell’Ateneo, Roma, kindly provided by Ludovico Slongo
La Regia Aeronautica - volume I: Dalla non belligeranza all'intervento – Nino Arena, 1981 USSMA, Rome kindly provided by Stefano Lazzaro
L'8^o Gruppo Caccia in due conflitti mondiali - Giuseppe Pesce, 1974 STEM Mucchi, Modena kindly provided by Stefano Lazzaro
Operation Compass 1940 - Jon Latimer, 2000 Osprey Publishing, Oxford, ISBN 1-85532-967-0, kindly provided by Ludovico Slongo
The Bristol Blenheim: A complete history – Graham Warner, 2002 Crécy Publishing Limited, Manchester, ISBN 0-947554-92-0
The Desert Air Force - Roderick Owen, 1948 Hutchinson, London, kindly provided by Ludovico Slongo
The Desert Air War 1939 – 1945 – Richard Townshend Bickers, 1991 Leo Cooper, London, ISBN 0-85052-216-1, kindly provided by Ludovico Slongo
The Gloster Gladiator - Francis K. Mason, 1964 Macdonald & Co. Ltd. London
Woody - A Fighter Pilot's Album - Hugh A. Halliday, 1987 Canav Books, Toronto, ISBN 0-9690703-8-1
Additional information kindly provided by Stefano Lazzaro and Ludovico Slongo.