The eponymous Penny is a former cheesemaker who fills her toastie – one we think is Sydney’s best – with a rotating cast of cheeses, though there’s always a cheddar (for sharpness) and a raclette (for meltiness). More cheese goes on the outside of the sandwich for crisp crunch.

AP Bakery doesn’t do things by the book – or by halves. Its toastie is a cheesy, disc-shaped thing resembling a fancy hot pocket, with a pizza dough exterior encasing layers of cheese, onion, pepper and lashings of mustard for a spicy little kick.

Mayflower wasn’t content with simply putting truffles inside its cheesy, gooey croque monsieur. This decadent number also comes with a generous serve of shaved truffle on top. It’s the most over-the-top toastie on this list – and worth stopping in for.

Turmeric fried eggplant and tamarind-tomato sauce are not your everyday jaffle fillings. But then again, owner-chef O Tama Carey has never been one to follow the rules. Her topnotch toasties – available at brunch from her Sri Lankan fine diner – are made with house kade paan, Sri Lanka’s national bread.

A classic, Indo-style mie goreng – but inside a toastie. They call it magic, but we say it’s just downright inspired. This place also turns the same trick with beef rendang curry. But if curry doesn’t cut it, there’s also a New York-style Reuben on the menu.

Andy Bowdy doesn’t pull punches when it comes to his Sydney-famous cakes. His toastie game is no different – come for the Lee Tran, filled with charred broccolini, chilli mayo, capers and lemon entangled in caciocavallo, a stretchy southern Italian-style cheese.

The winning trifecta of mushrooms, melty raclette and truffle mayo is an easy one to pick. But it’s the heat from the pickled jalapenos that really takes Brickfields’ staple toastie to a whole new level. It’s unlikely you’ll see this one leave the menu any time soon.

Soul Dining’s cafe-deli spinoff does a toastie worthy of that restaurant’s reputation for stylish and inventive Korean fare. The item in question piles on mozzarella and Mexican cheeses, along with fried kimchi and pulled pork. Plus, you get a cute little ramiken of house-made pickles on the side.

This two-level diner is influenced by the nameless street food stalls that sit under overpasses in India. Its main game is pakoras and chai, but it also does another, lesser-known Indian favourite: jaffles stuffed with fillings such as potato and peanut chutney.

Fluffy scrambled eggs, Wagyu beef, grilled prawns and taro wedged between butter-infused bread – these are toasties like you’ve never seen before. Grab them from one of five neon-lit locations around Sydney.

They look like old-school jaffles on the outside. But on the inside, you might be dealing with anything from cheese and Vegemite to the elements of an eggs Benedict. For the signature, order the Mushie Trip with ‘shrooms, spinach, sweet onion and two kinds of cheese.

If simplicity is the key to brilliance, then whoever came up with the idea to stick bolognaise sauce and cheese between two slices of bread – then toast it to a golden crunch – should be given a Nobel Prize. This is definitely one we’ll be re-creating at home.

This laid-back cafe is named after the purported inventor of the sandwich, which tells you something about how committed it is to the carb-y cause. The signature 12-hour beef cheek sandwich is piled with rocket, cheese, horseradish mayo and secret sauce, then toasted. And it’s so, so good.

“Classic, not basic” is this slick sandwich deli’s credo. That means hulking tuna melts and toasted sangas filled with scamorza, provolone and Greek graviera cheeses, plus onion relish and optional salami. Primo.

An occasional purveyor of the five-cheese toastie. That might sound excessive to some, but considering this bar and eatery is devoted to cheese (and wine), it’s safe to say this one’s worth its curds and whey. Keep an eye on the Bishops’ weekly specials for it.

The selection rotates often, but there’s always a cracking toastie on the menu at every Bourke Street location. It might be ham and cheddar with a lick of sweet mustard pickle, or smoked Wagyu, pickled cucumber and Russian dressing beneath a blanket of melted cheddar.

Bondi’s best toastie is a perfect – and perhaps unlikely – marriage of Gruyere and kimchi, slapped between two slices of dark rye. It comes with just the right amount of ooze and kick to make for an extremely satisfying two-hander.

On top of a roaring night-time trade, this Spanish-inspired wine bar by the Love, Tilly Devine team also opens for brunch on Sunday. On the menu are jamon, tetilla cheese and truffle toasties just like you’d find in Barcelona. They're made even better with a sherry-spiked Bloody Mary on the side.

Porteño’s humble little bakery always has a couple of toasties on offer. You might order one filled with a trio of mushrooms, kale pesto and provolone. Or another stuffed with pastrami, cabbage, dijon and mustard.