Some of the images below were sourced from Cuba Postal. Thanks for permitting me to use them here.
1914 Airplane and castle, 1 of 1, Scott E5 ✱ ✱ ✱
1927 Air, 1 of 1, SG 353, Scott C1 ✱ ✱
5c - Naval Aircraft Factory PN
1927 Airplane and castle, 1 of 1, Scott E6 ✱ ✱ ✱
1928 Lindbergh Commemoration. Optd LINDBERGH FEBRERO 1928, 1 of 1, SG 364, Scott C2 ✱
5c - Naval Aircraft Factory PN
1931 Air, 8 of 8, SG 376, 378-384, Scott C4-C11 ✱ ✱ ✱ P
All stamps depict the Fokker F.10
1931 Airmail stamps, 5 of 5, SG 385-389, Scott C12-C14, C14A, C15 ✱ ✱ ✱
All stamps depict the Ford Trimotor
1935 Air (overprint), 1 of 1, SG 400, Scott C16 ✱ ✱
10c - Fokker F.10
1935 Airplane and castle, 1 of 1, Scott E7 ✱ ✱ ✱
1936 Air, 3 of 4, Scott C18-C21 ✱ ✱
1938 Air (overprint), 1 of 1, SG 426, Scott C30 ✱ ✱
5c - Naval Aircraft Factory PN
1939 Experimental Rocket Post. Optd EXPERIMENTO DEL COHETE Postal ANO DE 1939, 1 of 1, SG 433, Scott C31 ✱ ✓
10c - Ford Trimotor
1948 Air, 1 of 1, SG 377, Scott C40 ✱ ✱ ✱ ✓
8c - Fokker F.10
1952 39th anniv of Florida-Cuba flight by A Parla, 2 of 2, SG 605-606, Scott C61-C62 ✱ ✱
8c - Curtiss Model D, 25c - Curtiss Model D
1953 Air, 4 of 4, SG 666-669, Scott C75-C78 ✱ ✱ ✱
8c - Lockheed Constellation, 15c - Lockheed Constellation, $ 2 - Lockheed Constellation, $ 5 - Lockheed Constellation
1953 Board of Accounts building, 1 of 2, SG 675, Scott C91 ✱ ✱
25c - Lockheed Constellation
1954 Planes, 11 of 11, SG 698-708, Scott C96-C106 ✱ ✱ ✱
1955 Air (Lockheed Constellation type of 1953), 2 of 2, Scott C120-C121 ✱ ✱ ✱
Both stamps depict the Lockheed Constellation
1955 International Philatelic Exhibition, Havana, 4 of 5, SG 748-752, Scott C122-C126 ✱ ✱ ✱
8c - Wright Flyer, 12c - Spirit of St Louis, 30c - Lockheed Constellation, 50c - Convair F-102 Delta Dagger
1956 Air, 1 of 1, SG 390, Scott C130 ✱ ✱ ✱
50c - Ford Trimotor
1957 30th Anniv of Inaug of Air Mail Services between Havana and Key West, Florida, 1 of 1, SG 841, Scott C172 ✱
1960 30th anniv of National Airmail service, 1 of 1, SG 960, Scott C214 ✱
1960 Airmail overprints, 2 of 2, SG 942-943, Scott C203-C204 ✱ ✱ ✱
12c - Fokker F.10
1960 Airmail overprints. "HABILITADO ENTREGA ESPECIAL 10c", 2 of 2, SG E961-E962, Scott E29-E30 ✱ ✱
10c on 20c - Ford Trimotor, 10c on 50c - Ford Trimotor
1961 Airmail overprints. "HABILITADO PARA 8c", 2 of 2, SG 992-993, Scott C224-C225 ✱ ✱ ✱
8c on 15c - Lockheed Constellation, 8c on 20c - Fokker F.10
1964 Anniversaries ms, 1 of 1, SG MS1152, Scott 883a ✱ ✱
50c - Ford Trimotor
1964 Anniversaries, 1 of 1, SG 1151, Scott 883 ✱ ✱
50c - Ford Trimotor
1965 Stamp Day, 1 of 2, SG 1217, Scott 957 ✱
1965 Cuban Transport, 1 of 8, SG 1310-1317, Scott 1064 ✱ ✱
20c - Ilyushin Il-18
1966 7th Anniv of Revolution, 1 of 5, SG 1318-1322, Scott 1065-1069 ✱ ✱
10c - Mikoyan-Gurevich MiG-21
1968 35th anniv of Seville-Camaguey flight by Barberan and Collar, 1 of 2, SG 1580-1581, Scott 1336 ✱ ✱
13c - Breguet 19
1968 Civil Activities of Cuban Armed Forces, 1 of 4, SG 1618-1621, Scott 1374 ✱ ✱
3c - Antonov An-2
1970 Sugar Production, 1 of 7, SG 1776, Scott 1538 ✱ ✱
2c - Antonov An-2
1971 35th anniv of Camaguey-Seville flight by Menendez Pelaez, 1 of 2, SG 1818-1819, Scott C247-C248 ✱ ✱
13c - Lockheed Model 8 Sirius
1971 World Meteorological Day, 2 of 4, Scott 1589-1592 ✱
1972 1st Anniv of Havana–Santiago de Chile Air Service, 1 of 1, SG 1938, Scott C249 ✱ ✓
1974 10th Anniv of Civil Aeronautical Institute, 2 of 5, SG 2157-2161, Scott 1925-1929 ✱ ✱ P
10c - Antonov An-2, 13c - Ilyushin Il-62
1976 15th anniv of Bay of Pigs invasion, 1 of 3, SG 2289, Scott 2057 ✱
1976 Expo '76, USSR. Modern Transportation, 1 of 1, SG 2310, Scott 2078 ✱ ✱ ✱ ✓
30c - Tupolev Tu-144
1977 50th Anniv of Cuban Air Mail, 6 of 6, SG 2405-2410, Scott 2160-2163, C263-C264 ✱ ✱ ✱ ✓
1c - Wright Flyer, 2c - Ford Trimotor, 5c - Sikorsky S-40, 10c - Douglas DC-4, 13c - Lockheed Constellation, 30c - Ilyushin Il-18
1979 50th Anniv of Cuban Airlines, 6 of 6, SG 2587-2592, Scott 2283-2288 ✱ ✱ ✱ ✓
1c - Ford Trimotor, 2c - Sikorsky S-40, 3c - Douglas DC-3, 4c - Bristol Type 175 Britannia, 13c - Yakovlev Yak-40, 40c - Ilyushin Il-62
1981 Creation of Armed Forces, 1 of 3, SG 2712, Scott 2406 ✱
1982 Exports, 1 of 10, SG 2794, Scott 2488 ✱ ✱
8c - Tupolev Tu-154
1983 Alberto Santos-Dumont issued for Brasiliana 1983 ms, 1 of 1, SG MS2903, Scott 2597 ✱ ✱ ✱ ✓
1p - Santos-Dumont 14-bis
1986 25th Anniv of Ministry of Transport, 1 of 1, SG 3187, Scott 2877 ✱ ✱
5c - Tupolev Tu-154
1988 Cubana Airlines Transatlantic Flights, 6 of 6, SG 3339-3344, Scott 3028-3033 ✱ ✱ ✱ ✓
2c - Douglas DC-4, 4c - Bristol Type 175 Britannia, 5c - Ilyushin Il-62, 10c - Bristol Type 175 Britannia, 30c - Ilyushin Il-62, 50c - Ilyushin Il-62
1990 Stamp Day, 1 of 2, SG 3522-3523, Scott 3214 ✱ ✱ ✓
1993 60th Anniv of Seville (Spain) - Camaguey (Cuba) Flight by Mariano Barberan and Joaquin Collar, 1 of 1, SG 3827, Scott C326 ✱ ✱ ✓
30c - Breguet 19
1994 50th anniv of ICAO, 1 of 1, SG 3932, Scott 3609 ✱ ✱ ✱
65c - Douglas DC-3
1995 Second World War Combat Planes, 5 of 5, SG 3974-3978, Scott 3651-3655 ✱ ✱ ✱ P
10c - Supermarine Spitfire, 15c - Ilyushin Il-2, 65c - Curtiss P-40 Warhawk, 75c - Messerschmitt BF 109, 85c - Morane-Saulnier M.S.406
1996 “Espamer” Spanish–Latin American and “Aviation and Space” Stamp Exhibitions, Seville, Spain, 4 of 4, SG 4058-4061, Scott 3727-3730 ✱ ✱ ✱ ✓
16c - Cierva C.4, 65c - CASA C-352, 75c - CASA C-201 Alcotán, 85c - CASA C-212 Aviocar
1997 Stamp Day. Postal Services, 1 of 2, SG 4160-4161, Scott 3823 ✱ ✱
65c - Fokker F.10
1999 70th anniv of Cubana, 4 of 4, SG 4380-4383, Scott 4041-4044 ✱ ✱ ✱ ✓
15c - Fokker F27 Friendship, 15c - McDonnell Douglas DC-10, 65c - Airbus A320, 75c - Douglas DC-3
2000 Stamp Day, 1 of 2, SG 4408-4409, Scott 4071 ✱
2003 Transport, 2 of 5, SG 4654-4658, Scott 4305-4309 ✱ ✱
2003 Centenary of powered flight, 4 of 4, SG 4707-4710, Scott 4357-4360 ✱ ✱ ✱ ✓
5c - Wright Flyer, 15c - Pitcairn Mailwing, 65c - Stearman C3, 75c - Douglas M-1
2004 75th Anniv of Cubana de Aviacion, 3 of 3, SG 4771-4773, Scott 4420-4422 ✱ ✱ ✱ ✓
15c - Lockheed Constellation, 65c - Ilyushin Il-62, 75c - Airbus A330
2006 Airplanes, 6 of 6, SG 4961-4966, Scott 4600-4605 ✱ ✱ ✱ ✓
10c - Granville Gee Bee, 15c - Bücker Bü 131 "Jungmann", 15c - Comte AC-4 Gentleman, 50c - North American P-51 Mustang, 75c - Supermarine Spitfire, 85c - Lavochkin La-9
2006 Airplanes ms, 6 of 6, SG MS4967, Scott 4606 ✱ ✱ ✱ ✓
1p - Bücker Bü 133 "Jungmeister"
2007 Philatelic championship s/s, 1 of 1, SG 5127, Scott 4762 ✱ ✱ ✱
1p - Ford Trimotor
2009 80th anniv of Cubana Airlines, 6 of 6, SG 5435-5440, Scott 5020-5025 ✱ ✱ ✱ ✓
5c - Ford Trimotor, 15c - Sikorsky S-38, 45c - Douglas DC-3, 50c - Douglas DC-4, 65c - Ilyushin Il-62, 75c - Ilyushin Il-96
2009 80th anniv of Cubana Airlines ms, 1 of 1, SG MS5441, Scott 5026 ✱ ✱ ✱ ✓
1p - Tupolev Tu-204
2010 Expo Shanghai, 6 of 6, SG 5517-5522, Scott 5115-5121 ✱ ✱ ✱
5c - Savoia-Marchetti S.55, 10c - Farman F.60 Goliath, 15c - Fokker D.VII, 45c - Koolhoven F.K.50, 65c - Junkers Ju 52, 85c - Latécoère 28
2010 Expo Shanghai ms, 1 of 1, SG MS5523 ✱ ✱ ✱ ✓
1p - Handley Page HP-42, 1p - Vickers Viscount
2011 Indipex, 6 of 6, SG 5605-5610 ✱ ✱ ✱ ✓
10c - Blériot XI, 15c - Stinson Detroiter, 20c - Lockheed Vega, 65c - Seversky P-35, 90c - Lockheed Model 10 Electra
2011 Indipex ms, 1 of 1, SG MS5611 ✱ ✱ ✓
1p - Curtiss Robin
2013 Key West - Havana flight, 1 of 1 ✱ ✱
2014 80th anniv of Cubana Airlines, 4 of 4 ✱ ✱ ✱ ✱
15c - Curtiss Robin, 20c - Bristol Type 175 Britannia, 45c - Lockheed Model 10 Electra, 75c - Antonov An-148
2015 11th National Stamp Championships, 1 of 1 ✱ ✱
65c - Spirit of St Louis
2016 55th anniv of the eastern army, 1 of 1 ✱
2016 Victims of terrorism, 1 of 1 ✱ ✱
2016 55th anniv of the western army, 1 of 1 ✱
2016 55th anniv of the Ministry of Transport, 1 of 1 ✱ ✱
2019 40th anniv of ANEC, 1 of 1 ✱ ✱
2020 100th anniv of the first commercial flight in Cuba, 1 of 1 ✱ ✱ ✱
90c - Farman F.60 Goliath
2021 60th anniv of the Ministry of Transport, 1 of 1 ✱ ✱
