[1] During his time on City Council, Dilkens chaired the International Relations Committee and the Essex Windsor Solid Waste Authority.

[5] Dilkens was criticized for promoting a $3 million dollar project to create a Christmas lights display amidst the mass flooding.

[22][23][24] In March 2022, Dilkens helped in securing a $5-billion investment for Canada's first domestic EV battery manufacturing facility.

[26] In June 2022, Dilkens joined Dongshin Motech Ltd. CEO Choon Woo Lim to approve their lease terms and Letter of Intent to build a $60-million, 170,000-square-foot manufacturing facility.

CAMPP, claiming thousands of supporters, promoted community involvement in the decision-making process, and "financially, socially and environmentally responsible sound urban planning principles".

[31] In 2019, Dilkens was criticized for social media comments which appeared to dismiss vandalism perpetrated against one of the CAMPP supporters.

[32] CAMPP was denied leave to appeal Ontario's Divisional Court in July 2020,[33] and the mega hospital will be built on the corner of County Road 42 and the 9th Concession.

"[33] In 2015, a petition garnering 12,000 signatures urged Dilkens to retract municipal approval for a commercial development near the Ojibway Prairie Complex.

Dilkens stated: "To move forward with closure of Matchette Road at this time would certainly have put this corporation in a great deal of jeopardy".

During the council meeting, security personnel removed several citizens who voiced their objection to a presentation by developer CoCo Paving.

[36] For the second year in a row, the City of Windsor earned an "A" from the Carbon Disclosure Project for its efforts on climate action in 2020.

Local charity and social workers criticized the move as "dehumanizing" and failing to address or understand poverty.

Dilkens defended his position, claiming that panhandling makes residents and families uncomfortable and stating that it is "incumbent upon us" to create a safe and welcoming environment downtown.

[40] In 2019, Dilkens was asked by local reporters his stance on an unsanctioned overdose prevention site, which had been set up to help combat the opioid epidemic.

[42] In 2019, Dilkens and City Council approved the purchase of 20 surveillance cameras for Downtown Windsor to monitor events in real-time and to help make modifications to traffic flow as needed.

This posed a major risk to the national economy, since the main access point to the Ambassador Bridge, which carries up to $450-million in trade with the United States every day, was choked off by the protestors.

[48] To support the ongoing police response to the blockade, Dilkens declared a state of emergency on February 14, which lasted 10 days.

"[50] On August 10, 2022, Dilkens was appointed by the Ontario government to serve as the chair of the Housing Supply Action Plan Implementation Team.