Windsor is a great Ontario city to live in as a sports fan. It just takes a quick 15 minute trip crossing the border into Detroit and all of a sudden you have access to professional sports teams from all four of the major North American sports leagues. I personally have stayed in Windsor on a sports trip to see the Lions and Red Wings live over the course of a weekend.

Sports betting has grown tremendously in Ontario over the past decade, and Windsor is no exception. With Ontario legalizing and regulating sports betting, it has become the norm for Windsor residents to place wagers on a wide variety of sporting events throughout the year, and I expect this trend to continue in the coming years.

Best Sportsbooks for Windsor Residents

  • 1 See Website For Details
    • Licensed and regulated in Canada
    • Easy deposits & withdrawals including Interac
    • Competitive betting lines
    Bet Now Review
  • 2 #Ad
    • Most popular betting site worldwide
    • State of the art live betting platform including streaming of several events
    • Fixed odds for horse racing
    Bet Now Review
  • 3 See Website For Details
    • Licensed in Ontario and Malta (accepts bettors from across Canada)
    • Competitive betting lines
    • Easy deposit/withdrawal options, including Interac
    Bet Now Review

These are our three top rated betting sites for Ontario residents. All three sportsbooks are licensed by iGaming Ontario to operate in the regulated Ontario gambling market. is our #1 rated site. They are completely focused on the Canadian market, which shows through in their easy to use betting platform, deposit/withdrawal options for Canadians (including Interac), and customer service. Check out our full SIA review here.

Land-Based Retail Sportsbooks In Windsor

Caesars Windsor is located right on the river in downtown Windsor. Caesars Windsor is the first casino in Ontario to add a full-service retail sportsbook. The Caesars Sportsbook launched in January of 2023 with betting counters and kiosks taking bets on professional sports at the front of Legends Sports Bar in the Casino. The betting counters are open 7 days a week from 10am to midnight, while the betting kiosks are open 24/7.

Offline Sports Betting in Windsor

Offline sports betting in Windsor is also available through Proline, which is the sports betting lottery offered by the Ontario government. You can check out our OLG and Proline pages to see how I feel about this betting option. Basically the odds provide far worse value to the player than the online betting sites listed above.

My #1 tip for Ontario residents who bet through Proline is to make the jump to placing your wagers through any of the betting sites I’ve listed above. If you are a winning bettor you will see your profit improve significantly and if you’re currently losing money at Proline you may even break even or at least lose less by wagering at the fair odds provided by the betting sites.

Leamington Raceway

The Windsor Raceway closed in 2012 so there is no horse racing location within the city, but both Northville Downs and Leamington Raceway are about 45 minute drives from the city center.

For the purposes of this page I will take a closer look at Leamington Raceway because it doesn’t require crossing the border into the United States.

The track offers live harness racing every Sunday throughout the racing season, with betting on the races available at the track.

Major Sports Teams Near Windsor

Windsor is directly across the river from Detroit, so its very easy for Windsor residents to cross the border and see professional sporting events in Detroit. I personally have stayed in Windsor in order to watch Lions or Red Wings games across the river.

  • Detroit Lions (NFL)
  • Detroit Red Wings (NHL)
  • Detroit Detroit Pistons (NBA)
  • Detroit Tigers (MLB)