
#1 Benefit
Last year’s top-tier foodie event—including the biennial silent auction—netted $3 million for research at the University Health Network. About 775 generous diners supped on chef-cooked meals at the homes of 30 Toronto philanthropists. This year, a non-auction year, about 400 supporters are expected to attend. Next: October 27, 2018

#2 Benefit
With a new name, a more celebratory tone and a move to Thursday night from Tuesday, the gala in support of Right to Play expects 1,200 patrons to raise more than $2 million this year. National Bank of Canada and Power Corporation are title sponsors, and four-time Canadian Olympic hockey champion Caroline Ouellette will be honored. Next: October 11, 2018

#3 Benefit
The fund-raiser for veterans and military families honored women in uniform last year and raised $1.5 million. This year’s cocktails-and-dinner soiree, at the Metro Toronto Conference Centre, marks the event’s 10th anniversary, and 1,100 supporters are expected. Bell returns as the presenting sponsor, along with CTV and National Post. Next: November 8, 2018

#4 Benefit
Some 850 people dined and danced in support of the Children’s Aid Foundation of Canada at the 2017 edition of the gala. Business newscaster Amanda Lang co-hosted at the Metro Toronto Convention Centre where IT and business consulting services firm GCI was the patron partner, with Scotiabank and TD also lending support. Next: October 27, 2018

#5 Benefit
This sit-down dinner on the field at the Rogers Centre grew to 1,500 guests in 2018, including the full Blue Jays roster. More than $1.5 million was raised for the benefit of children and youth in the Jays Care programs across Canada. Sponsors included Rogers, Cisco, and Samsung. Next: June 2019

#6 Benefit (up from #8)
Rebranded with a one-word name and a new venue for 2018 at the Evergreen Brickworks, the gala for Reach, which advocates for youth with disabilities, is aiming to match its 2017 fund-raising take of $500,000. The gala dinner will again be followed by the Crystal Club after party for charitable Toronto millennials. Next: November 3, 2018

#7 Benefit
The 2017 edition of DXI changed venues, to the former Unilever soap factory, and doubled in size because it also celebrated the inaugural opening of EDIT: The Expo for Design, Innovation and Technology. Attendance this year, back at the Design Exchange, is expected to return to normal size of about 1,000 guests. Next: November 8, 2018

#8 Benefit
The theme for the 20th anniversary celebrations was Carousel, with the Power Plant gallery reimagined as a carnival-esque adult fun land, filled with naughty and provocative artistic installations. More than 1,300 people attended, although the event did not sell out, and about $360,000 was raised. Max Mara returned as the presenting sponsor. Next: June 2019

#9 Benefit
Returning to the lakefront Corus Quay, the benefit for Second Harvest’s food rescue program raised about $900,000 this year—enough to provide 1.8 million meals to Torontonians in need. The sold-out, al fresco event featured more than 60 chefs and 30 beverage purveyors, and CI Financial joined as a new sponsor. Next: June 2019

#10 Benefit
Rebranded from Rally for Kids with Cancer, and now in support of the Pinball Clemons Foundation for marginalized kids in Canada and abroad, this celebrity-infused car rally aims to raise over $850,000 this year. Platinum Cars comes on board as a new sponsor in 2018. Next: October 26-27, 2018

#11 Benefit
After moving to the Art Gallery of Ontario in 2017 and increasing attendance to 400, the small-plates, food- and wine-tasting event and auction raised a record $349,000 for the Stop Community Food Centre. Stonegate Private Counsel and Fiesta Farms are sponsors for 2018, again at the AGO. Next: November 7, 2018

#12 Benefit
The multi-venue dinner party, at boutiques on Yorkville’s Mink Mile, plans to add five new retailer/restaurants this year, for a total of 20, and top 2017’s fund-raising total of $700,000. The after-party, for next-gen supporters of the Canadian Foundation for AIDS Research, will be bigger than ever this year, when BMO returns as the signature partner. Next: November 28, 2018

#13 Benefit
The sold-out fund-raiser for conservationists moved to the waterfront Rebel nightclub in 2018, increased attendance to 450, and raised more than $500,000. This year’s highlight was a tribute to Swim Drink Fish board member Gord Downie, who passed away in 2017, and a performance by his former Tragically Hip bandmate Paul Langlois. Next: April 2019

#14 Benefit
After a performance by members of the National Ballet, 1,800 patrons enjoyed a cocktail reception, with 650 of them proceeding to a V.I.P. dinner on stage at the Four Seasons Centre. The event raised $1.3 million and had a disco theme. CIBC returned as lead sponsor for the 12th consecutive year. Next: June 19, 2019

#15 Benefit (up from #16)
A sold-out event for science-minded socialites grew to maximum capacity at the Ontario Science Centre last year, with 510 patrons raising $662,000 net for the organization’s community programs. RBC remains the title sponsor. Next: November 15, 2018

#16 Benefit (up from #18)
The Massive Illusion, at the Art Gallery of Ontario, sold out in 2018, when 1,800 guests raised more than $320,000 for the institution’s public programming and learning activities. Highlights included a total of five DJs spinning tunes and plenty of food and drink. Google and Grolsch sponsored. Next: April 16, 2019

#17 Benefit
Cartier hosted the sold-out dinner for 170 V.I.P. patrons this year, which preceded the performance and 1,000-person party at the Four Seasons Centre for the Performing Arts. The theme this year was Into the Stars, inspired by the Canadian Opera Company’s upcoming world premier of Rufus Wainwright’s opera Hadrian. Next: May 16, 2019

#18 Benefit (new to the list)
The reinvented Book Lovers’ Ball, in support of the Toronto Public Library Foundation’s programs for at-risk youth, returned after a year’s hiatus with a new name and a sold-out crowd of 470 raising more than $700,000. The party, which took place in the dolled-up Toronto Reference Library, was sponsored by TD Bank Group and Toronto Life magazine. Next: April 2019

#19 Benefit
With a theme of Wild West, the youthful celebration returns to the Rebel nightclub this year, hoping 1,800 guests will raise about $500,000 to fight breast cancer. H&M joins as the event’s new national apparel sponsor in 2018. Next: October 12, 2018

#20 Benefit
For the 10th edition of the fund-raiser in support of Canadian literacy, a capacity crowd of 400 culture mavens, creative types, and C.E.O.s packed the Distillery District’s Fermenting Cellar and raised $470,000. New table sponsors included Facebook and Queen’s University. Next: January 23, 2019