Jason Blake knocked home a bouncing puck with less than five minutes remaining against his former team, and the Maple Leafs held on for a 3-2 victory on Wednesday.
Roloson stole a win the last time New York visited Toronto, stopping 58 shots on Nov. 23. The Islanders were a little unfortunate this time as Blake's winning goal came when the puck hit fellow forward Mikhail Grabovski's skate in the corner and squirted in front.
Francois Beauchemin and Ian White also had goals for Toronto (10-13-7).
The Maple Leafs were left with little time to savor the win before their focus shifted to the Bruins, who will host Toronto on Thursday. Boston beat the Maple Leafs 7-2 on Saturday.
"I'm glad we're playing the Bruins again," Maple Leafs coach Ron Wilson said. "We can't play any worse than we did the last time."
It means even more to Phil Kessel, in his first season with Toronto after starting his career with Boston. Kessel is facing his former team for the second time in a span of six days, and had his worst game of the season in the previous meeting.
"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."
Toronto came dangerously close to blowing Wednesday's game after appearing in control through 40 minutes.
The Leafs had a 2-0 lead heading into the third period, but allowed Islanders rookie John Tavares to score twice on the power play. Blake scored after Grabovski pressured Mark Streit, prompting the Islanders defenseman to turn over the puck.
"I had some other opportunities in the game that didn't pan out," Blake said. "You've just got to keep working and stay positive, hopefully get a bounce. Fortunately, it went in."
Tavares, the No. 1 pick in this year's draft, had both goals for the Islanders (11-13-7) for the second straight night, but neither effort was enough for a win. New York was beaten 6-2 at Philadelphia on Tuesday.
The 19-year-old Tavares, an Ontario native, has 15 goals in 31 games.
"It's good to contribute, but at the end of the day it really doesn't matter a whole lot," Tavares said. "It's too bad we weren't able to at least get the point."
Roloson wasn't tested nearly as much during this visit to Toronto. Maple Leafs coach Ron Wilson was hoping for an early goal to keep him from feeling "invincible" in the building.
He got his wish after Matt Moulson took the first of two minor penalties in the opening period.
Beauchemin one-timed Tomas Kaberle's pass through traffic that beat Roloson between the legs at 6:04. It was Toronto's first power-play goal in five games.
The Leafs went ahead 2-0 just one second after Moulson stepped out the penalty box following his second penalty. Ian White scored his fifth goal of the season by wiring a shot over Roloson's right pad at 14:40.
That provided a seemingly comfortable lead over the Islanders, who finished a stretch in which they played 14 of 17 on the road.
Toronto's Vesa Toskala wasn't tested much through 40 minutes, although he made a couple nice saves on Kyle Okposo in the second period.
The game tightened after the Islanders were given a lengthy 5-on-3 period early in the third period. Tavares scored his first of the night by scoring from in close at 1:32.
He pumped his left fist after netting a goal against his favorite childhood team for the first time. It didn't take long for the second.
Tavares tied it 2-2 at 11:54 on another Islanders power play, tapping home a nice pass from Okposo. All four of his goals in his two-night spurt were scored from about five feet away from the net. He leads NHL rookies in goals.
"He's found a home in that spot off the side of the net, and he's been able to bury them," Islanders coach Scott Gordon said. "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."
The Maple Leafs had a power-play opportunity shortly after, but couldn't get a shot past Roloson. Blake, who played for the Islanders from 2001-07 before signing with Toronto, scored his fifth of the season at 15:55.
The Maple Leafs, who started 0-7-1, are 6-2 since their loss to the Islanders last month, and have moved within five points of eighth place in the Eastern Conference.
"We have to put our foot on the gas and play our best hockey every night," Blake said. "Last game when we played in Boston, we didn't do that."
Leafs D Jeff Finger was a healthy scratch for the second straight game. ... Toronto D Luke Schenn played his 100th NHL game. ... Tavares got caught out for a shift that lasted more than two minutes in the second period.