On 14 September 2020, six men were arrested and charged for historic sex and drug offences alleged to have taken place at the school from the 1970s to the early 2000s.

[12] On 11 November 2020, former Assistant Principal Ian Wilson pleaded guilty to two charges involving indecent acts while working at Dilworth.

Wilson had earlier been convicted of doing an indecent act with a boy under 12 years in 1996 while serving as Senior School Assistant Principal at MacMurray Boarding House.

[13] In late November, it was reported that a former 69-year old Scout Master, whose named was suppressed, facing charges of indecently assaulting a boy in the 1970s had died from cancer.

[15] On 22 December, Detective Senior Sergeant Geoff Baber reported that an additional 80 victims had been identified and that 33 charges had been filed against five men aged between 68 and 78 as part of Operation Beverly.

[16] On 10 February 2021, Police identified a former scout master who died before he could face two separate trials for historical sexual offending as Richard Charles Galloway.

[17] On 23 March 2021, former assistant principal Ian Robert Wilson was sentenced by Judge Russell Collins at the Auckland District Court to three years and seven months in prison.

[22] On 31 March 2022, former tutor Jonathan Peter Stephens was sentenced to six months' home detention, having earlier pleaded guilty to two charges of indecently assaulting a boy.

[26] Dilworth established a process for redress for historic physical and sexual abuse and budgeted $44 million to be paid out to up to 250 survivors.

In 2024, it was reported that the school had revised upwards the number of former students entitled to redress and was subsequently expecting to pay out $55 million.

[27] On 18 September 2023, an independent inquiry into sexual and physical abuse at Dilworth between 1950 and 2005 led by Dame Silvia Cartwright and Frances Joychild KC released its report.

Cartwright and Joychild's inquiry concluded that "ongoing silence about the sexual abuse recorded in this report is the primary reason for the damage caused to many former students at Dilworth.

In 2015, Dilworth made history by beating Onehunga High School, 12–10, in a 1A Championship promotion match and entered Auckland's top-flight for the first time in 109 years.

In 2016, Dilworth lost much of their starting line-up, however, managed to win three crucial matches against Otahuhu 43–3, Onehunga 19–7 and Kelston Boys' 26–14 to secure an 8th-place finish and survival in the 1A.

The following weekend, Dilworth produced one of the biggest upsets in 1A history, beating 2016 National Champions and 2017 World Championship silver medallists, Mount Albert Grammar, 20–15.

After respectable 2017 and 2018 campaigns avoiding relegation, a noteworthy feat for the league's smallest school with a roll of just over 300,[39] in 2019, Dilworth finished the season in the drop zone.

However, in their relegation match, they won emphatically, downing One Tree Hill 95–0 to secure a sixth consecutive berth in 1A rugby for 2020.

[40] The school's basketball programme has also enjoyed success and defeated some of the country's powerhouse programs to be finalists in the Auckland Premier league in both 2007 and 2008.

[41] As of July 2019, the Ministry of Education reported 68.9% of the school roll was Māori or Pasifika whilst 21.9% of pupils were European and 6.7% of Asian descent.