The Backup Plan: How Winnipeg Ended Its 29-Year Grey Cup Drought

On November 29, 2015, the Grey Cup was played in Winnipeg for the first time in 24 years. The hometown Blue Bombers were not in it. They had finished 5-13, dead last in the West Division, watching Edmonton beat Ottawa 26-20 at Investors Group Field from the wrong side of the turnstiles.

A decade later, the Grey Cup returns to Winnipeg — Princess Auto Stadium, November 16, 2025 — and the Bombers are again fighting for their season with a quarterback question hanging over the roster. Zach Collaros has been ruled out against the Toronto

Argonauts, and once again the Winnipeg Blue Bombers are asking a backup quarterback to hold a season together.

They have been here before — and not only in 2015. In 2019 it was Matt Nichols who went down, Chris Streveler who stepped in, and Kyle Walters who went out and traded for Zach Collaros in October, a move that produced a Grey Cup six weeks later. The difference is the calendar. In 2015 the Bombers were playing out a lost season. In 2025 they are playing for the right to still be in the building when the Grey Cup is handed out on November 16.

That 2015 season is worth remembering for what it wasn't. Drew Willy, the franchise quarterback the Bombers had bet on, went down with a knee injury early, and Winnipeg spent the summer auditioning replacements — Brian Brohm, Robert Marve, a rotating cast of arms — before Walters sent a conditional draft pick to Edmonton for Matt Nichols on September 2. It didn't matter. The Bombers finished 5-13, last in the West, out of the playoffs for a fourth consecutive year, and Mike O'Shea — two seasons into a head-coaching career, coming off a 7-11 step backward — spent Grey Cup week as a spectator in his own stadium.

The Grey Cup that November belonged to Edmonton and Ottawa: Mike Reilly outduelling Henry Burris 26-20, Reilly named the game's MVP, Burris left to wonder what might have been after a Most Outstanding Player season. Winnipeg watched it happen on its own turf, from the wrong side of the turnstiles, and the image stuck. A city that had not won a championship since 1990 and had not hosted a Grey Cup since 2006, reduced to landlord.

What happened next is the reason this November matters. O'Shea and Walters kept their jobs. The draft classes got better. By 2016 the Bombers were back in the playoffs; by 2017 and 2018 they were in the West Final; and in 2019 they ended the drought — 33-12 over Hamilton in Calgary, a 29-year wait finally over. Two years later they did it again, 33-25 in overtime against the Tiger-Cats at Tim Hortons Field, with Collaros under centre and a second Most Outstanding Player award to follow in 2022.

Then came the part that still stings. Four straight Grey Cup appearances from 2021 through 2024, and three straight losses to close them out: 24-23 to Toronto in Regina, 28-24 to Montreal in Hamilton, 41-24 to the Argonauts again in Vancouver. The best team in the West for half a decade, and still one Sunday short, every single time.

So the Grey Cup returns to Winnipeg on November 16, 2025, to a stadium that has been renamed twice since that 2015 afternoon — Investors Group Field, then IG Field, now Princess Auto Stadium — and to a franchise that has spent ten years proving the distance between last place and the last Sunday in November can be closed. Collaros is 37 now. The offensive line has been rebuilt around him. The West has gotten younger, and the margin for error has gotten thinner with every season.

Which is why the word out of the quarterback room lands the way it does. Ten years ago, Winnipeg watched a Grey Cup it hosted and could not reach. This time, the Bombers have a decade of evidence that the gap can be crossed — and a quarterback question that has followed this franchise all the way from the wrong side of the turnstiles back to the centre of the CFL's biggest stage.