From the bench clearing brawls to the postseason pressures, these two teams have been through it all.
As we enter the final months of the regular season, fans look forward to the entertainment that these matchups bring.
With Boston currently sitting fourth in the AL East, however, they've got their work cut out for them if they hope to play deep into October.
Will Boston's lack of contention late in the season affect the Yankees' postseason run?
Let's take a look.
Regardless of record, the Red Sox and Yankees will always play each other tough.
The Red Sox currently rank fourth in the AL East, nine games behind the Bronx Bombers.
The Yankees-Red Sox rivalry squares off nine more times before the end of the season, giving fans their fill of late season entertainment.
The first series starts in just over a week, with the last two meetings coming in mid-September and early October.
If the BoSox are struggling late in the season, they may surrender the Yanks a few big wins to help them clinch their playoff berth.
If they are in contention, they will only push the Yankees that much harder to earn their playoff bid while asserting their dominance over Beantown.
These games will put enough pressure on the division-leading Yanks to solidify their spot at the top of the standings.
In addition to those meetings, the Blue Jays are still scheduled for another 12 matchups with the Bombers before season’s end.
They currently sit at the bottom of the AL East, but are just five games off the Wild Card leaders and still in the playoff hunt.
The Jays may be 10 games back from the Yanks in the division, but that isn’t to say they are a team that can be taken lightly.
The Yankees aren’t the type of team to play down to their opponent.
Every time these guys put on that uniform, they expect a victory.
The rich history and culture that surrounds Yankee baseball is enough to push this team to another level when the time calls for it.
If you think they are going to lie down and die due to a lack of pressure because the Red Sox aren’t contenders, then you are sorely mistaken.
Out of their 54 remaining games, 48 come against teams that are currently within five games of a playoff spot.
That’s one tough road to October, so you can count on an intensely focused Yankee team down the home stretch.