In this OLG Winners series, we’re highlighting the real winning stories of everyday Ontarians who played the lottery. From paying it forward to making long-held dreams a reality, these winners show us what they’re doing with their new fortunes – and how one win can bring joy, hope and even a fresh start.

As we head towards March Break, the start of the new school year can feel like a distant memory. But for one Ontario woman, late August of 2025 is a time she’ll never forget.

Jessica, a school bus driver for children with special needs, was enjoying the end of her calm, quiet summer. She was in her room, dozing off with her cat on her lap, when her phone buzzed. It was a notification from the OLG app.

Like many other Ontarians, Jessica bought her lottery ticket online. It’s a simple process: You create an account at OLG.ca, load up your e-wallet, and play your favourite lotteries and games, all from the comfort of your phone.

And, if you do win a prize, you get notified directly after the draw with a message sending you to check your online account. No need to check a ticket at a physical location.

That’s exactly what happened with Jessica, who’s from Etobicoke.

A few weeks prior, she’d gone online and had bought herself an extra treat for her 50th birthday: A QUICK PICK LOTTO 6/49 ticket with ENCORE – one of her go-to games.

“I’m a sporadic OLG player, on and off for the last decade,” she says. “I’ve always just thrown [ENCORE] on the ticket.”

Jessica had forgotten about her birthday ticket until she saw the notification on her phone.

She leaped up, her cat nearly falling off her lap, and grabbed her phone. The OLG app had told her that she had won.

“No way,” she recalls saying, and ran to tell her husband of 26 years the news. Jessica had matched six of seven numbers with ENCORE and won $100,000.

ENCORE is a bonus game that can be added to draw games such as LOTTO 6/49 or LOTTO MAX games for just $1. It offers 22 extra ways to win prizes ranging from $2 to $1 million.

Jessica and her husband couldn’t wait to tell their family the news. She says they were shocked and excited about what this win would mean for them.

“We told them all to play the lottery,” she says. That’s exactly what Jessica tells everyone who hears her news: “[Like] what [OLG] ads say all the time, ‘You gotta play it to win it!’”

How does Jessica feel about having won? “Amazing,” she says. “Surreal is probably the most apt description.”

As for her plans with her $100,000 winnings, Jessica will take this opportunity to bulk up her savings and manage her finances for the future.

The children on her school bus, whom she picks up and drops off every day, will be happy to hear they’ll continue to be greeted by her smiling face. “I’m still going to be driving my route,” she says.

“She’s a beast behind the wheel,” her husband says affectionately. He’s referring to her confidence, care and commitment to keeping the children safe, comfortable and right on schedule.

Except now? She’s six-figures richer.

Don’t miss your chance to celebrate big milestones with OLG. Get your tickets at OLG.ca or in-store today.