The Blue Jays swept the series, caught the Yankees two weeks later and claimed their first division title since 1993.
This year, the roles are reversed and the Yankees will look to inch closer to the Blue Jays when the teams open a three-game series on Monday night at Yankee Stadium.
The Blue Jays outscored the Yankees 10-1 during its three-game sweep last Aug. 7-9 at Yankee Stadium, won nine of the final 13 meetings and the American League East by six games. The Blue Jays have continued to do well against the Yankees this year by winning seven of the first nine meetings.
All of those meetings took place in the first two months of the season when the Yankees were still struggling to recover from a dreadful 9-17 start. Eventually, New York's inability to fully recover led to four trades around the non-waiver deadline, but selling off veterans has the opposite effect for the Yankees.
The Yankees (60-57) have won eight of their last 13 games and are within 4 1/2 games of Boston for the second wild card and 6 1/2 games behind Toronto.
New York was unable to keep pace with either team and was handed a 12-3 loss Sunday afternoon by the Tampa Bay Rays.
The last meeting against Toronto was June 1 and 10 players on New York's 25-man roster are currently not on the active roster.
Three of the notable names who are on the roster are Gary Sanchez, Tyler Austin and Aaron Judge. When the Yankees last faced Toronto, Sanchez was recovering from a thumb injury, Judge was hitting .224 in Triple-A and Austin was batting .259 in Double-A.
Sanchez is batting .275 (11-for-40) in 10 games while splitting time between catcher and designated hitter. Judge homered for the second straight day and is the second Yankee to do so in his first two major league games.
They were part of a lineup with eight players under 27, marking the first time since Oct. 1, 1967, that the Yankees fielded a lineup that young.
"You know, I'm just trying to go out there and do a job and get on base for the team," Judge said. "I was comfortable Day One. I've just got to keep it going."
Now Judge and the Yankees will try to do it against one of the best teams in the American League for the last two months.
Toronto had a .500 record when it began its three-game sweep of New York. The Blue Jays have had a winning record since they were 40-25 after Troy Tulowitzki, Russell Martin and Edwin Encarnacion homered in a 9-2 win over the Houston Astros on Sunday.
"We hit some homers," Toronto manager John Gibbons said. "That's what we do best. The key is to get guys on base and then pop one here and there. We've been (in a) little lull for a little over two weeks. I just stress that it's a matter of time."
The Blue Jays have 166 home runs, but 17 in the last 13 games. Since its sweep against the Yankees last August, Toronto's power has not hit a lull as it has 28 home runs in the last 22 games against the Yankees.
R.A Dickey is scheduled to start for Toronto and has drastic splits for road and home games. In Toronto, he is 2-8 with a 5.57 ERA in 13 starts, but outside of Canada he is 6-4 with a 3.51 ERA in 11 starts.
One of those road starts was May 24 in New York when Dickey allowed four runs and five hits in 6 2/3 innings of a 6-0 loss. Dickey had a 4.60 ERA after falling to 7-5 lifetime against the Yankees. Since then, his ERA has stayed the same thanks to allowing at least four earned runs in four of his last five starts.
Chad Green will start for the Yankees and is among those young players to experience struggles especially as a starting pitcher. The right-hander is 1-2 with a 7.50 in four starts in the majors and was demoted after allowing three runs and eight hits in 3 2/3 innings on Aug. 3 against the New York Mets.
With Triple-A Scranton/Wilkes Barre, Green is 7-6 with a 1.52 ERA in 16 games.
"I think all players hit bumps, whether you're young or old," Yankees manager Joe Girardi said. "But one thing I think part of our focus has to be is helping those kids get through those bumps because you don't get here unless you're talented enough."