They're two of an array of food and wine figures from across Australia pairing up at the Melbourne Food and Wine Festival in convivial Perfect Match sessions to challenge the wine-matching status quo and explore exciting – and sometimes unlikely – couplings. Each of these casual, sit-down sessions includes up to nine wines, three dishes and banter between the presenters about food, wine, and each other.

In the case of D'Sylva, he is owner-chef of two acclaimed Melbourne restaurants – South East Asian-inspired Coda and Indian-accented Tonka – known almost as well for their wine lists as their food. Singh's Avani Syrah, grown at her cool-climate biodynamic vineyard at Red Hill in Victoria, has garnered plaudits from critics around the country for its intensity and character. Both are keen to debunk the widespread myth that spicy subcontinental dishes don't marry well with wine.

Singh's career has included mentoring from Bass Phillip's Phillip Jones and many years as co-proprietor, with her husband Devendra, of well-regarded Mornington Peninsula Indian restaurant Tulsi. The wine and food pairing that has surprised and delighted her most in the past couple of years is sangiovese – or cool-climate shiraz – with dhal.

"Dhal is usually cooked with tomato, garlic, onion and light spices. Both the lentils and (sangiovese or cool-climate shiraz) have earthy flavours which go well together. The good acidity in the wine balances the sweetness of the onion and tomato in the dish, and also brings out the sweet fruit characteristics in the wine."

D'Sylva, recently returned from a stint cooking in Delhi, says his Melbourne sommelier, Travis Howe, "serves me all kinds of stuff to pair with our menu ranging from South African chenin blanc to benchmark Barolo."

"Basic rules with Indian food are: don't mix chilli with tannins, off-dry whites with spice work, and – as always – good acid in a bottle will help refresh the palate and cut through some of the more challenging dishes."

Expect more myth-busting from the Mildura-based pairing of alternative wine variety champion Kim Chalmers of Chalmers Wines and Jim McDougall, head chef at the eponymous Jim McDougall in Stefano's Cellar. Red wine with fish? Sure, says McDougall.

"The most interesting match we've made in the last few years was a pinot noir with Murray cod, which was garnished with roast-chicken sauce and bone marrow. The reason it was a successful match is because cod, like barramundi or monkfish, lends itself to meaty flavours, so it can be accompanied with a soft, aromatic red wine."

Chalmers likes to explore the possibilities of lesser-known varieties, citing a McDougall dish of camp oven rabbit stew coupled with Chalmers 2014 Aglianico Rosato as her happiest food-pairing surprise of recent months. "The smokiness and light game flavours of the rabbit worked perfectly with the creamy texture and charry barrel ferment characters of the wine. The perceived fruit sweetness of the dry rosato was highlighted by the sweet slow-cooked pearl onions in the stew and herbal-savoury characters in the wine were tied into the dish with bay leaf and woody herbs."

What wine-and-food furphy would Chalmers most like to debunk? "Red wine and cheese. There are some exceptions, but generally red wine and cheese is not a great combination.  I'd always go for a fortified, sticky or even a white over a red wine with cheese."

Wine writer Matt Skinner will moderate the series: session presenters include Ben Sears and Eun Hee An from Sydney hotspot Moon Park, who will join winemaker Brad Hickey to match Brash Higgins wines from McLaren Vale to new-wave Korean. Seafood guru John Susman teams with Supernormal sommelier Leanne Altmann to demonstrate why shellfish and wine is among the happiest of marriages.

Victor Liong of Melbourne's Lee Ho Fook and winemaker Bill Downie will put up playful interpretations of Chinese dishes, while Raph Rashid of Beatbox Kitchen, Taco Truck and All Day Donuts will join wine writer Mike Bennie to show that street-food hook-ups don't stop at burgers and beer or tacos and tequila.

Says D'Sylva: "Forget preconceived notions of what should go with what. You don't need red wine with red meat, nor white wine with white meat. Think of matching strong flavours with strong wines, light flavours with light wines and figure out what works for you."

Acqua Panna Perfect Match, 28 February – 1 March, Melbourne Town Hall, $85