The history of the pressurised cabin is not very well documented. This feature was mostly experimental in the 1930's, saw some use during WW2 and was widespread after 1945. Here is an attempt at listing all pressurised aircraft until 1945. This list is certainly incomplete, additions and corrections are welcome.
I've included some projects before 1939 that seemed significant, but I won't attempt to list every wartime project because they are too numerous. Aircraft under parentheses were not completed or did not receive pressurisation equipment.
It is probable that some of the WW2 military aircraft listed, notably the single-seat fighters, only had a low pressure differential (partial pressurisation) as opposed to the high pressure differential found on an airliner. I would be interested to learn more about these details too.
1920 (?) Packard-Lepère LUSAC-11
The Wikipedia page on cabin pressurisation mentions an oxygen-enriched airtight cabin, not pressurised, allowing to dispense with the use of oxygen masks. I've not found any other reference to the airtight cabin, or pictures of the aircraft.
This aircraft broke two world altitude records, at 10093 m by Rudolf Schroeder on Feb. 27, 1920, and at 11145 m by John Macready on Sep. 28, 1921.
1921 Engineering Division USD-9A
The USD-9A was an Airco DH.9A modified by Engineering Division at McCook Field. Some examples were also made by Dayton-Wright. One aircraft was fitted with a pressurised cabin and tested in 1921 by Harold Harris.
1931 Junkers Ju 49
Experimental aircraft.
1932 Farman 1000
Experimental aircraft.
1932 (Guerchais 110)
Experimental aircraft. One prototype was almost completed but the engine and perhaps the cabin were never installed.
http://www.secretprojects.co.uk/forum/index.php?topic=18632.5
1933 (Caproni Ca.117)
Experimental aircraft project.
1935 Farman 1001
Experimental aircraft, like the Farman 1000 with parasol wing.
1935 Chizhevski BOK-1
Experimental aircraft, derived from the ANT-25 long-range aircraft.
1936 Farman 1002
Experimental aircraft, evolution of the Farman 1001. No picture is known.
1936 Chizhevski BOK-7
Experimental aircraft, evolution of the BOK-1.
1937 Junkers EF.61
Experimental two engine aircraft.
1937 Farman F.223.1
Four engine transport with rubberized semi-airtight cabin and oxygen enrichment.
1937 Chizhevski BOK-11
Reconnaissance aircraft, evolution of the BOK-1 and BOK-7.
1937 Chizhevski BOK-15
Long-range aircraft, evolution of the BOK-1 and BOK-7.
1937 Lockheed XC-35
Two engine research aircraft, derivative of the Lockheed 10 Electra with a pressurised cabin.
1938 Renard R.35
Three engine commercial transport, crashed during its first flight.
1938 Boeing 307 Stratoliner
Four engine commercial transport, the first pressurised aircraft to enter commercial service.
1938 (Douglas DC-4E)
Four engine commercial transport. Cabin pressurisation was planned but not installed on the prototype.
1938 Caproni Ca.161 bis
Single engine biplane, with a tiny pressurised cabin (almost like an oversize scaphander) for a record flight to 17083 m.
1938 (SNCAC NC.140)
Four-engine bomber project.
1939 (Caproni Ca.340)
Altitude record project.
http://www.secretprojects.co.uk/forum/index.php/topic,11932.msg129171.html#msg129171
1939 Henschel Hs 128
Two engine experimental aircraft.
1939 Farman/SNCAC NC.2230 / NC.223.4
Four engine transport with rubberized semi-airtight cabin and oxygen enrichment.
1939 SNCAC NC.130
Two engine experimental aircraft.
1939 SNCAC NC.150
Two engine prototype bomber, with a third engine inside the fuselage driving the compressors.
1940 Henschel Hs 130 A
Two engine reconnaissance aircraft, developed from the Hs 128.
1940 Junkers Ju 86 P
Two engine bomber and reconnaissance aircraft, high-altitude version of the Ju 86.
1940 Junkers Ju 288
Two engine bomber and reconnaissance aircraft.
1940 Arado Ar 240
Two engine multi-purpose aircraft (fighter, night fighter, light bomber and reconnaissance).
1940 Vickers 407/421/431 Wellington V & VI
Two engine bombers, pressurised variants of the Wellington.
1940 Curtiss CW-20
Two engine commercial transport, prototype of the C-46. It was designed for cabin pressurisation, but I don't know if the pressurisation system was actually installed. It seems that military C-46 were not pressurised.
1941 (DFS 54)
High altitude experimental glider with pilot in prone position. The cabin was built but the rest of the aircraft was unfinished. The project later evolved as the DFS 228.
1941 Piaggio P.111
Two engine experimental aircraft.
1941 Supermarine Spitfire Mk.VI
Single-seat fighter.
1942 Henschel Hs 130 C
Two engine bomber and reconnaissance aircraft, developed from the Hs 130 A but quite different.
1942 Henschel Hs 130 E
Two engine bomber and reconnaissance aircraft, evolution of the Hs 130 A with a third engine inside the fuselage driving the compressors.
1942 Dornier Do 217 P
Two engine bomber and reconnaissance aircraft, high altitude version of the Do 217 with a third engine inside the fuselage driving the compressors, an installation similar to the Hs 130 E.
1942 Focke-Wulf Fw 191
Two engine bomber and reconnaissance aircraft, for the same program as the Ju 288 and Do 317.
1942 Junkers Ju 86 R
Two engine bomber and reconnaissance aircraft, a further high-altitude version of the Ju 86.
1942 Arado Ar 440
Two engine multi-purpose aircraft, evolution of the Ar 240.
1942 Messerschmitt Bf 109 G-1, G-3, G-5
Single-seat fighter.
1942 (Piaggio P.108 C)
Four engine commercial transport. The pressurisation equipment was perhaps never installed.
1942 Tachikawa A-26 / Ki-77
Two engine long-range aircraft with an unpressurised airtight cabin and oxygen enrichment. The system was a failure and the crew had to wear oxygen masks throughout the flights.
1942 Supermarine Spitfire Mk.VII
Single-seat fighter.
1942 Westland Welkin
Two engine fighter, built on a specification drafted after the Ju 86 P started to fly over Britain.
1942 Vickers Type 432
Two engine fighter, competitor of the Westland Welkin.
1942 North American NA-63 / XB-28 Dragon
Two engine bomber, derivative of the B-25.
1942 Boeing B-29 Superfortress
Four engine bomber, certainly the most successful pressurised bomber of WW2.
1942 Consolidated B-32 Dominator
Four engine bomber, competitor of the B-29. The pressurisation system was removed in subsequent variants.
1942 Bell P-59 Airacomet
Two engine jet fighter.
1943 Dornier Do 317 V1
Two engine bomber and reconnaissance aircraft, competitor of the Ju 288 and Fw 191. Only the first prototype flew with cabin pressurisation, which was abandoned on the later five aircraft.
1943 Junkers Ju 388
Two engine bomber and reconnaissance aircraft.
1943 Arado Ar 234
Two or four engine jet bomber and reconnaissance aircraft. Cabin pressurisation was installed on several variants, but not all.
1943 Focke-Wulf Ta 154
Two engine fighter.
1943 Tachikawa SS-1
Two engine experimental aircraft, modification of a Tachikawa Type LO, itself a license-built version of the Lockheed 14 Super Electra.
1943 De Havilland Mosquito NF.XV, B.XVI, PR.XVI, PR.32, PR.34, B.35
Two engine jet fighter.
1943 Vickers 447/457/461 Windsor
Four engine prototype bomber, developed from the Warwick.
1943 Lockheed L-049 / C-69 Constellation
Four engine transport aircraft.
1944 DFS 228
Experimental reconnaissance aircraft, with rocket engine and pilot in prone position.
1944 Blohm & Voss BV 155 B
Single engine fighter prototype.
1944 Focke-Wulf Ta 152 H
Single engine fighter.
1944 (Junkers Ju 290 A/B)
Four engine transport and bomber. The normal versions were not pressurised. A special pressurised transport was planned as the Ju 290 A-6, but the aircraft was finished without pressurisation. The first prototype of the Ju 290 B-1 bomber was also intended to have a pressurised flight deck and turrets, but flew without the pressurisation equipment.
1944 Tachikawa Ki-74
Two engine bomber and reconnaissance aircraft.
1944 Kawasaki Ki-108
Two engine fighter prototype.
1944 Supermarine Spitfire PR Mk.X, PR Mk.XIX
Single-seat reconnaissance aircraft.
1944 Boeing C-97 Stratofreighter
Four engine transport aircraft.
1944 Lockheed P-80 Shooting Star
Single engine jet fighter.
1945 (Tachikawa Ki-94 II)
Single engine fighter prototype, was completed but did not fly.
1945 Nakajima Ki-87
Single engine fighter prototype.
1945 Messerschmitt Me 163 C
Rocket interceptor, evolution of the Me 163 B (which did not have cabin pressurisation).
1945 Messerschmitt Me 263 / Junkers Ju 248
Rocket interceptor, further evolution of the Me 163.
1945 Gloster Meteor F.4
Two engine jet fighter. The F.4 was the first version of the Meteor with pressurised cockpit, and flew right before the end of the war.
1945 Avro Type 688 Tudor
Four engine transport, which flew right before the end of the war.
1945 Bell XP-83
Two engine jet fighter.
1945 Heinkel He 274
Four engine bomber, developed in 1944 and flown in France in 1945, after the end of WW2.
1946 SNCAC NC.3021 Belphégor
Single engine experimental aircraft, designed in the early 1940s. It flew only in 1946, at a time when the design was already antiquated.
I've included some projects before 1939 that seemed significant, but I won't attempt to list every wartime project because they are too numerous. Aircraft under parentheses were not completed or did not receive pressurisation equipment.
It is probable that some of the WW2 military aircraft listed, notably the single-seat fighters, only had a low pressure differential (partial pressurisation) as opposed to the high pressure differential found on an airliner. I would be interested to learn more about these details too.
1920 (?) Packard-Lepère LUSAC-11
The Wikipedia page on cabin pressurisation mentions an oxygen-enriched airtight cabin, not pressurised, allowing to dispense with the use of oxygen masks. I've not found any other reference to the airtight cabin, or pictures of the aircraft.
This aircraft broke two world altitude records, at 10093 m by Rudolf Schroeder on Feb. 27, 1920, and at 11145 m by John Macready on Sep. 28, 1921.
1921 Engineering Division USD-9A
The USD-9A was an Airco DH.9A modified by Engineering Division at McCook Field. Some examples were also made by Dayton-Wright. One aircraft was fitted with a pressurised cabin and tested in 1921 by Harold Harris.
1931 Junkers Ju 49
Experimental aircraft.
1932 Farman 1000
Experimental aircraft.
1932 (Guerchais 110)
Experimental aircraft. One prototype was almost completed but the engine and perhaps the cabin were never installed.
http://www.secretprojects.co.uk/forum/index.php?topic=18632.5
1933 (Caproni Ca.117)
Experimental aircraft project.
1935 Farman 1001
Experimental aircraft, like the Farman 1000 with parasol wing.
1935 Chizhevski BOK-1
Experimental aircraft, derived from the ANT-25 long-range aircraft.
1936 Farman 1002
Experimental aircraft, evolution of the Farman 1001. No picture is known.
1936 Chizhevski BOK-7
Experimental aircraft, evolution of the BOK-1.
1937 Junkers EF.61
Experimental two engine aircraft.
1937 Farman F.223.1
Four engine transport with rubberized semi-airtight cabin and oxygen enrichment.
1937 Chizhevski BOK-11
Reconnaissance aircraft, evolution of the BOK-1 and BOK-7.
1937 Chizhevski BOK-15
Long-range aircraft, evolution of the BOK-1 and BOK-7.
1937 Lockheed XC-35
Two engine research aircraft, derivative of the Lockheed 10 Electra with a pressurised cabin.
1938 Renard R.35
Three engine commercial transport, crashed during its first flight.
1938 Boeing 307 Stratoliner
Four engine commercial transport, the first pressurised aircraft to enter commercial service.
1938 (Douglas DC-4E)
Four engine commercial transport. Cabin pressurisation was planned but not installed on the prototype.
1938 Caproni Ca.161 bis
Single engine biplane, with a tiny pressurised cabin (almost like an oversize scaphander) for a record flight to 17083 m.
1938 (SNCAC NC.140)
Four-engine bomber project.
1939 (Caproni Ca.340)
Altitude record project.
http://www.secretprojects.co.uk/forum/index.php/topic,11932.msg129171.html#msg129171
1939 Henschel Hs 128
Two engine experimental aircraft.
1939 Farman/SNCAC NC.2230 / NC.223.4
Four engine transport with rubberized semi-airtight cabin and oxygen enrichment.
1939 SNCAC NC.130
Two engine experimental aircraft.
1939 SNCAC NC.150
Two engine prototype bomber, with a third engine inside the fuselage driving the compressors.
1940 Henschel Hs 130 A
Two engine reconnaissance aircraft, developed from the Hs 128.
1940 Junkers Ju 86 P
Two engine bomber and reconnaissance aircraft, high-altitude version of the Ju 86.
1940 Junkers Ju 288
Two engine bomber and reconnaissance aircraft.
1940 Arado Ar 240
Two engine multi-purpose aircraft (fighter, night fighter, light bomber and reconnaissance).
1940 Vickers 407/421/431 Wellington V & VI
Two engine bombers, pressurised variants of the Wellington.
1940 Curtiss CW-20
Two engine commercial transport, prototype of the C-46. It was designed for cabin pressurisation, but I don't know if the pressurisation system was actually installed. It seems that military C-46 were not pressurised.
1941 (DFS 54)
High altitude experimental glider with pilot in prone position. The cabin was built but the rest of the aircraft was unfinished. The project later evolved as the DFS 228.
1941 Piaggio P.111
Two engine experimental aircraft.
1941 Supermarine Spitfire Mk.VI
Single-seat fighter.
1942 Henschel Hs 130 C
Two engine bomber and reconnaissance aircraft, developed from the Hs 130 A but quite different.
1942 Henschel Hs 130 E
Two engine bomber and reconnaissance aircraft, evolution of the Hs 130 A with a third engine inside the fuselage driving the compressors.
1942 Dornier Do 217 P
Two engine bomber and reconnaissance aircraft, high altitude version of the Do 217 with a third engine inside the fuselage driving the compressors, an installation similar to the Hs 130 E.
1942 Focke-Wulf Fw 191
Two engine bomber and reconnaissance aircraft, for the same program as the Ju 288 and Do 317.
1942 Junkers Ju 86 R
Two engine bomber and reconnaissance aircraft, a further high-altitude version of the Ju 86.
1942 Arado Ar 440
Two engine multi-purpose aircraft, evolution of the Ar 240.
1942 Messerschmitt Bf 109 G-1, G-3, G-5
Single-seat fighter.
1942 (Piaggio P.108 C)
Four engine commercial transport. The pressurisation equipment was perhaps never installed.
1942 Tachikawa A-26 / Ki-77
Two engine long-range aircraft with an unpressurised airtight cabin and oxygen enrichment. The system was a failure and the crew had to wear oxygen masks throughout the flights.
1942 Supermarine Spitfire Mk.VII
Single-seat fighter.
1942 Westland Welkin
Two engine fighter, built on a specification drafted after the Ju 86 P started to fly over Britain.
1942 Vickers Type 432
Two engine fighter, competitor of the Westland Welkin.
1942 North American NA-63 / XB-28 Dragon
Two engine bomber, derivative of the B-25.
1942 Boeing B-29 Superfortress
Four engine bomber, certainly the most successful pressurised bomber of WW2.
1942 Consolidated B-32 Dominator
Four engine bomber, competitor of the B-29. The pressurisation system was removed in subsequent variants.
1942 Bell P-59 Airacomet
Two engine jet fighter.
1943 Dornier Do 317 V1
Two engine bomber and reconnaissance aircraft, competitor of the Ju 288 and Fw 191. Only the first prototype flew with cabin pressurisation, which was abandoned on the later five aircraft.
1943 Junkers Ju 388
Two engine bomber and reconnaissance aircraft.
1943 Arado Ar 234
Two or four engine jet bomber and reconnaissance aircraft. Cabin pressurisation was installed on several variants, but not all.
1943 Focke-Wulf Ta 154
Two engine fighter.
1943 Tachikawa SS-1
Two engine experimental aircraft, modification of a Tachikawa Type LO, itself a license-built version of the Lockheed 14 Super Electra.
1943 De Havilland Mosquito NF.XV, B.XVI, PR.XVI, PR.32, PR.34, B.35
Two engine jet fighter.
1943 Vickers 447/457/461 Windsor
Four engine prototype bomber, developed from the Warwick.
1943 Lockheed L-049 / C-69 Constellation
Four engine transport aircraft.
1944 DFS 228
Experimental reconnaissance aircraft, with rocket engine and pilot in prone position.
1944 Blohm & Voss BV 155 B
Single engine fighter prototype.
1944 Focke-Wulf Ta 152 H
Single engine fighter.
1944 (Junkers Ju 290 A/B)
Four engine transport and bomber. The normal versions were not pressurised. A special pressurised transport was planned as the Ju 290 A-6, but the aircraft was finished without pressurisation. The first prototype of the Ju 290 B-1 bomber was also intended to have a pressurised flight deck and turrets, but flew without the pressurisation equipment.
1944 Tachikawa Ki-74
Two engine bomber and reconnaissance aircraft.
1944 Kawasaki Ki-108
Two engine fighter prototype.
1944 Supermarine Spitfire PR Mk.X, PR Mk.XIX
Single-seat reconnaissance aircraft.
1944 Boeing C-97 Stratofreighter
Four engine transport aircraft.
1944 Lockheed P-80 Shooting Star
Single engine jet fighter.
1945 (Tachikawa Ki-94 II)
Single engine fighter prototype, was completed but did not fly.
1945 Nakajima Ki-87
Single engine fighter prototype.
1945 Messerschmitt Me 163 C
Rocket interceptor, evolution of the Me 163 B (which did not have cabin pressurisation).
1945 Messerschmitt Me 263 / Junkers Ju 248
Rocket interceptor, further evolution of the Me 163.
1945 Gloster Meteor F.4
Two engine jet fighter. The F.4 was the first version of the Meteor with pressurised cockpit, and flew right before the end of the war.
1945 Avro Type 688 Tudor
Four engine transport, which flew right before the end of the war.
1945 Bell XP-83
Two engine jet fighter.
1945 Heinkel He 274
Four engine bomber, developed in 1944 and flown in France in 1945, after the end of WW2.
1946 SNCAC NC.3021 Belphégor
Single engine experimental aircraft, designed in the early 1940s. It flew only in 1946, at a time when the design was already antiquated.
