Jeffrey's Philly Cheese Steak is not your average steak sandwich—this is premium quality done right. We start with a full five-ounce rib-eye steak, cooked to tender perfection and sliced thin. Topped with sautéed onions and green peppers that add sweetness and crunch, then smothered in melted Swiss cheese. But what truly sets our Philly apart is our house-made basil and oregano aioli that brings an herby, garlicky richness to every bite. All of this is piled high on a garlic toasted bun that's sturdy enough to hold this magnificent sandwich together. For over 40 years, we've been serving quality American pub food in Winnipeg, and this Philly showcases exactly why Jeffrey's has stood the test of time.
The difference between an okay Philly cheese steak and a truly great one comes down to quality ingredients and proper execution—and at Jeffrey's Restaurant & Lounge, we don't cut corners on either. Our version starts with a genuine five-ounce rib-eye steak, the same cut you'd order at a steakhouse. We cook it to tender, juicy perfection, then slice it thin while it's still hot so every piece is bursting with flavor. This isn't processed steak product or mystery meat—it's quality rib-eye that you can taste in every bite.
The magic happens when we sauté fresh onions and green peppers until they're perfectly tender and slightly caramelized, bringing natural sweetness that complements the savory steak. We pile this hot mixture high and immediately top it with Swiss cheese, letting the heat melt it into gooey perfection. But the real secret weapon is our house-made basil and oregano aioli—a creamy, herby, garlicky spread that we prepare fresh. It adds layers of flavor that elevate this from a simple steak sandwich to something truly memorable. The garlic toasted bun provides the perfect vehicle, with just enough structure to hold everything together while adding its own subtle garlic flavor. Served with your choice of fresh-cut fries or Caesar salad, this sandwich embodies the quality and care that has made Jeffrey's a Winnipeg institution for over 40 years. Whether you're dining in our sports bar watching the Jets game, enjoying live music on the weekend, or ordering takeout, this is a sandwich that delivers steakhouse quality in a casual pub setting.
* One of our most popular sandwiches for 40+ years
Google Review
"Jeffreys is amazing! The dine-in service is excellent and the food is consistently excellent. We have been trying lots of different things on their menu - steak sandwich, burgers, pizza, nachos, steak wrap, etc - and everything has been delicious!"
August 17, 2025
Regular Customer
"This Philly cheese steak is the real deal! You can tell they use quality rib-eye - it's tender and so flavorful. The aioli is amazing, really takes it to another level. Best steak sandwich I've had in Winnipeg. This is why Jeffrey's has been around for 40 years!"
August 5, 2025
Food Critic
"I've had Philly cheese steaks all over North America and Jeffrey's version is outstanding. The rib-eye is legit quality meat, the vegetables are fresh and perfectly sautéed, and that house-made aioli is genius. This is pub food elevated to an art form!"
July 20, 2025
Located on Henderson Highway in East Kildonan. Serving premium quality pub food for over 40 years with live music on weekends.