The 2014 competition had five rounds proper before quarter-finals, semi-finals, and a final. The final, played on 7 September 2014, was won by Christchurch club Cashmere Technical, who beat Central United 2–1 for their second trophy in two years, the first club to go back to back since 1998. The Jack Batty Memorial Cup for man of the final was won by Cashmere Technical's Stu Kelly.
All teams listed below received byes to the second round.
Northern Region: Albany United, Auckland University, Beachlands Maraetai, Cambridge, Claudelands Rovers, Eastern Suburbs, Ellerslie, FC Whangarei, Fencibles United, Forrest Hill-Milford United, Hibiscus Coast, Lynn-Avon United, Mangere United, Manurewa, Melville United, Metro, Mt. Albert-Ponsonby, Ngongotaha, North Shore United, Onehunga-Mangere United, Oratia United, Otahuhu United, Otumoetai, Papakura City, Papatoetoe, Takapuna, Taradale, Tauranga City United, Te Atatu, Waiheke United, Waitemata City, Waiuku, Warkworth, Western Springs
Central/Capital Region: Brooklyn Northern United, Douglas Villa, Eastbourne, Havelock North Wanderers, Island Bay United, Marist Palmerston North, Marist Wellington, Miramar Rangers, Naenae, Napier City Rovers, North Wellington, Petone, Red Sox Manawatu, Seatoun, Stokes Valley, Stop Out, Tawa, Victoria University, Wainuiomata, Wairarapa United, Wanganui Athletic, Waterside Karori, Wellington Olympic, Wellington United, Western Suburbs
Mainland/Southern Region: Burwood, Canterbury University, Cashmere Technical, Central Pirates, Christchurch United, Coastal Spirit, Dunedin Technical, FC Nelson, Ferrymead Bays, Halswell United, Invercargill Old Boys, Invercargill Thistle, Melchester Rovers, Mosgiel, Nomads United, Northern, Northern Hearts, Otago University, Parklands United, Pleasant Point, Queens Park, Queenstown Rovers, Richmond Athletic, Selwyn United, Southend United, Waihopai, Waimakariri United, West End, Western
All teams listed below received byes to the third round.
Northern Region: Bay Olympic, Birkenhead United, Central United, East Coast Bays, Glenfield Rovers, Hamilton Wanderers, Ngaruawahia United, Onehunga Sports, Three Kings United, Waitakere City
Central/Capital Region: Lower Hutt City, Palmerston North End, Upper Hutt City
Note: Mangere had won the match 5–4 on penalties after it finished 3-all at the end of extra time, however the result was overturned after they were found to have fielded an ineligible player. Mangere appealed the decision, delaying the next two rounds matches before New Zealand Football came to a decision to forfeit the match and declare a 3–0 win to Hamilton Wanderers.
Note: The match was originally meant to be played on Sunday 15 June but Mangere United appealed the original decision to award Hamilton Wanderers the win in the previous round. After the appeal didn't result in the decision being overturned, the game was rescheduled for Sunday 29 June.