The transformation of Little Portugal has always revealed itself in the bars lining Dundas St. W. Sometimes 10 to a block between Ossington and Lansdowne Aves., there are whiskey and wine bars, gay bars and bars stocked with old-fashioned arcade games, bars in basements and bars with no name. Late-night drinkers can go door-to-door on a winter’s night, barely needing to don their coats.

It’s fitting, then, that this stretch of road should have served as the cradle for a new kind of watering hole, perhaps more incongruous and stranger than all the others: the hipster sports bar.

The strip now boasts no fewer than four such establishments, complete with kitschy memorabilia, artisanal variations on wings and nachos, and Raptors fans dressed like lumberjacks.

At first blush, a hipster sports bar seems like an oxymoron: on the one hand, a cultural subgroup dedicated to all things ironic and underground; on the other, a venue for watching the game with your bros. But at this late date in the history of hipsterdom, just such a hybrid has emerged.

The genre seems to have been born in American meccas of cool like Brooklyn (Mulholland’s) and Portland (Spirit of 77). Fashion-forward former New York Ranger Sean Avery opened Warren 77, which was described at the time as a “hipster sports bar,” in Tribeca a full five years ago.

The trend has migrated to Toronto only in the last year or so.

Three Dundas sports bars have opened since November 2013: The Contender, just west of Ossington Ave., The Dock Ellis, just west of Dovercourt Rd., and The Derby, just west of Dufferin St.

The fourth, Opera Bob’s — just east of Ossington Ave. — will celebrate six years in February.

But the horn-rimmed glasses crowd only began showing up recently, said manager Tommy Harlocker, a high-spirited man with tattoos covering his forearms.

“Before this bar was hipster anything, this was just a place to come and watch sports,” he said recently, while a Raptors game played.

Opera Bob’s is also the official bar of Toronto’s Manchester City FC fan club, as the rows of powder blue scarves and cleats lining a high shelf at the back of the bar can attest.

English soccer rowdies may not be the most genteel clientele, but regular patron Matt K. said Opera Bob’s is far more low-key than your typical sports bar.

A look at the strip

Tablet users, tap here to see a map of the strip on Dundas St. W.

Down the street at The Derby, a group of old university buddies from Western University had gathered to watch a late game between the Raptors and the Portland Trailblazers. (The Dock Ellis was full, they said.) Old football posters hung on one wall, showing a leather-helmeted running back stiff-arming an imaginary defender under the words, “Welcome Visitors.”

Brent Bogucki, who lives nearby, said he was relieved to have a familiar place to watch basketball.

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The Derby is small and cosy and, apart from the Muhammad Ali photo hanging on one wall, it looks like a regular cocktail lounge.

The same cannot be said for The Contender, the largest and most representative of the new hipster sports bars. A great cavernous beer hall, it’s densely packed with retro paraphernalia, specializing in posters of neglected fan favourites such as former Raptors Matt (The Red Rocket) Bonnerand Jerome (Junkyard Dog) Williams.

Erin and Pam, two friends on a girls’ night out, were puzzled by the Iraqi soccer scarf displayed above a row of seats.

“These are hipster jocks,” said Pam, looking around her at the men in topknots and flannel shirts, tattoos festooning their skin. “Are these hipster jocks?”

“Do you think any of these dudes have played basketball in the last five years?” said Erin.

Pam noticed the dessert poutine on the chalkboard menu and said the beer selection here seemed better than at most sports bars.

Erin agreed. “If they have Molson, it’s ironically.”

The Dock Ellis does not have Molson. Named after the late Pittsburgh Pirates pitcher of the late ’60s and early ’70s, who claims to have thrown a no-hitter while tripping on acid, the bar prides itself on serving independent Ontario brewers. It opened in November 2013 and, in many ways, The Contender and The Derby have modelled themselves in its image.

“[Hipsters] like sports, too,” said co-owner Alain Pitout on a recent night in the bar’s basement, which hosts a recreational darts league when it isn’t used as an escape valve for the perpetually packed main room upstairs.

“They just wanted somewhere comfortable to hang out where they didn’t feel awkward and uncomfortable and unwelcome.”

Pitout and his fellow owners — Andrew Kaiser and Callum Woods, bar industry veterans — consciously cultivated a hipster esthetic, lining the walls with vintage baseball pennants and a shuffleboard table, along with more typical Toronto sports bric-a-brac (a signed picture of Brett Lawrie and a framed Nazem Kadri jersey take pride of place). The menu, by chef Trish Gill, changes every month

“We wanted to veer away from the cookie cutter,” said Pitout.

“We were jokingly going to call it ‘Hipster Sports Bar.’ ”