This edition was on the 3rd & 4th May. It was the last edition to have the flying display held on 1 day. Special guests included Ryan Campbell and Doctor Paul Bevilaqua.
It also featured for the 1st time the Showtime Freestyle Motocross shows, which featured the most experienced freestyle motocross team in Australia, with an average of 250 performances a year, 4 of which were at the 2014 air show. They later returned in 2018.
The adjunct Illawarra Light Railway Museum was also added to the show for the 1st time.
The below flying program shows what was scheduled before the event began. When the event began, weather, mechanical issues with the aircraft or military requirements may have amended the program in its final displayed form at the Airport.
- 9am – Gates Open
- 10:15am – Caribou (take-off)
- 10:30am – F/A-18 Hornet (x2) (Arrival)
- 10:35am – The Red Berets (Official Air Show Opening)
- 10:40am – Pitts S1S (Paul Bennet)
- 10:50am – Caribou
- 10:55am – L39 Albatros
- 11:05am – Boeing Stearman
- 11:15am – Extra 300L (Matt Hall)
- 11:25am – Wirraway
- 11:35am – T6 Texan
- 11:45am – Super “Connie” Constellation
- 11:55am – Spitfire
- 12:05pm – Marchetti S211
- 12:15pm – Jet Provost
- 12:30pm – NSW Ambulance/CHC Helicopters AW139 (Winching Display)
- 12:45pm – Jet Car
- 12:55pm – Catalina
- 1:10pm – Piper J-3 Cub
- 1:25pm – C47, P51 Mustang & P40 Kittyhawk
- 1:35pm – P40 Kittyhawk
- 1:45pm – P51 Mustang
- 2pm – Avenger
- 2:10pm – Squirrels
- 2:20pm – L39 Albatross
- 2:30pm – Hudson
- 2:40pm – Bell UH-1″Huey” Iroquois
- 2:50pm – Sabre ***(Air Show Debut)***
- 3pm – F/A-18 Hornet (x2) (Display/Departure)
- 3:15pm – The Royal Australian Air Force Roulettes
- 3:30pm – Air Show Concludes
- 5pm – Gates Close
- 6:45pm – Swing Into Wings Begins
- 7:15pm – Swing Into Wings Dinner
- 10pm – Swing Into Wings Ends
Swing Into Wings – Victory In Europe
Organised by the Rotary Club of Illawarra Sunrise, the 2014 dinner was once again held in the Australian Aerial Patrol hanger. It cost $80 to attend. The event had a cash bar and raffle with music by The Big Brass Sounds of Short and Horny. Proceeds went to local Rotary charities including the Australian Aerial Patrol & the Salvation Army First Floor programme.