Jason Blake squeezed a shot past Roloson at 15:55 of the third period Wednesday as the Maple Leafs edged the Islanders 3-2.
Roloson stole a victory the last time he visited Air Canada Centre, making 58 saves on Nov. 23. The Maple Leafs were left with little time to savour a victory in his return here as they travelled to Boston immediately after the game and will face the Bruins on Thursday night.
They have even more unfinished business with their Original Six rival following a 7-2 loss at TD Garden on Saturday night.
"I'm glad we're playing the Bruins again," said Leafs coach Ron Wilson. "We can't play any worse than we did the last time."
It was sentiment echoed by forward Phil Kessel, who will face his former team for the second time in a span of six days. He had his worst game as a Maple Leaf during the last visit to Boston.
"I struggled," he said. "I don't think I can go in there again and struggle like that. ... We've got to go in and win."
The Leafs came dangerously close to blowing Wednesday's game against the Islanders after appearing in control through 40 minutes.
They had a 2-0 lead heading into the third period, but allowed John Tavares to score twice on the power play and tie things up. Blake's winner came after Mikhail Grabovski pressured Mark Streit on the forecheck, prompting the Islanders defenceman to turn the puck over. The Leafs forward made no mistake.
"I had some other opportunities in the game that didn't pan out," said Blake. "You've just got to keep working and stay positive, hopefully get a bounce. Fortunately, it went in."
Francois Beauchemin and Ian White also scored while Vesa Toskala made 30 saves for Toronto (10-13-7), which moved within two points of the 11-13-7 Islanders in the Eastern Conference standings.
Even though Tavares increased his rookie goal-scoring lead to 15, there was little solace in getting a pair against the team he grew up cheering for.
"It's good to contribute, but at the end of the day it really doesn't matter a whole lot," said Tavares. "It's too bad we weren't able to at least get the point. There were some positives, but we've definitely got a lot to work on."
Roloson wasn't tested near as much during this visit to Toronto.
Wilson was hoping for an early goal to keep the goalie from feeling "invincible" in this building and got his wish after Matt Moulson took the first of two minor penalties in the opening period. Beauchemin one-timed a Tomas Kaberle pass through traffic that beat Roloson between the legs at 6:04.
It was the team's first power-play goal in five games.
Toronto went ahead 2-0 just one second after Moulson stepped out the penalty box after serving his second minor. White got his fifth goal of the season by wiring a shot over Roloson's right pad at 14:40.
That looked like it would be enough against an Islanders team that was not only playing for the second time in as many nights, but was also wrapping up a stretch where it played 14 of 17 games on the road.
Tavares brought his team back to life in the third period. He tied it 2-2 at 11:54, tapping home a nice cross-ice pass from Kyle Okposo for his fourth goal in two nights - all of them scored from no more than five feet away from the net.
"He's found a home in that spot off the side of the net and he's been able to bury them," said Islanders coach Scott Gordon. "It's good to see because early in the season he had a few opportunities that he didn't cash in on and I know he was frustrated, but he's finding them now."
After starting the season with an ugly 0-7-1 record, the Leafs have started to find some victories. They are 6-2-0 since losing to the Islanders on Nov. 23 and find themselves within five points of eighth spot in the Eastern Conference.
With a game against the Bruins looming, they're focused on climbing even closer.
"We have to put our foot on the gas and play our best hockey every night," said Blake. "Last game when we played in Boston, we didn't do that. ...
"We have to make sure we're ready to go (on Thursday night)."
Notes: Leafs defenceman Jeff Finger was a healthy scratch for the second straight game ... Martin Biron dressed as the backup goalie for the Isles. Rick DiPietro is on a conditioning stint with AHL Bridgeport ... It was the first time all season Toronto won two in a row at home ... Luke Schenn played his 100th career NHL game for the Leafs ... Tavares got caught out for a shift that lasted more than two minutes in the second period ... Announced attendance was 19,102.