The New York Yankees have won 27 World Series titles, while the Boston Red Sox have nine championships to their name. But the bitter rivals are dead even when it comes to playoff matchups, and one looks to take the first step toward gaining the upper hand on Tuesday.
The seventh postseason meeting between the American League East adversaries begins when the Red Sox (87-75) visit Yankee Stadium to take on the Yankees (93-68) at 8 p.m. ET in Game 1 of their AL Wild Card Series. The teams also squared off in this round last year, with New York winning the series 2-1.
That triumph tied the clubs at three wins apiece in playoff matchups. The Yankees also defeated the Red Sox in the 1999 and 2003 AL Championship Series, while Boston was victorious in the 2004 ALCS, the 2018 AL Division Series and the AL Wild Card Game in 2021.
New York took the regular-season series in 2026, finishing with a 7-6 record after outscoring Boston 25-3 in winning the final two games. The Yankees won four of their six matchups in the Bronx.
If New York hopes to advance to the ALDS, it will have to get past Boston without three-time AL MVP Aaron Judge, who was left off the team's wild card roster. The slugger, who returned to the club on Sept. 8 after missing more than three months with a fractured rib, was placed back on the injured list just eight days later with a strained right calf.
AL Cy Young Award favorite Cam Schlittler (14-6, AL-best 1.95 ERA) will start for New York. The 25-year-old right-hander went 2-1 with a minuscule 0.74 ERA in four turns against the Red Sox this year. He will be opposed by left-hander Payton Tolle (9-6, 3.03), who hasn't lost since July 1 (5-0 in 13 outings) and gave up one run over 13 innings while going 1-0 in two starts against the Yankees in 2026.
A National League Wild Card Series also begins Tuesday night as the San Diego Padres (91-71) host the Chicago Cubs (89-73) at 10 p.m. ET at Petco Park. The Cubs dominated the season series between the clubs, winning the final five games after dropping the opener. Chicago outscored San Diego 32-10 over the final two contests.
Right-hander Michael King (12-10, 3.21) will be on the mound for the Padres. The 31-year-old posted a 2.74 ERA at home this year and allowed a total of five runs across 32 innings while going 4-0 over five starts before yielding five in four frames of a loss to the Los Angeles Dodgers in his regular-season finale. Chicago counters with southpaw Matthew Boyd (10-5, 3.91), who won his final two turns and went 1-0 in two starts against San Diego despite surrendering eight runs over nine innings.
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The 2026-27 NHL season gets underway on Tuesday with five games, including an "Original Six" matchup between the Montreal Canadiens and Toronto Maple Leafs at 7 p.m. ET at Scotiabank Arena. The teams are opening the season against each other for the seventh consecutive time, with Toronto posting the victory in four of the previous six campaigns. After suffering a 5-2 loss at Toronto in their 2025-26 opener, the Canadiens won the final three meetings between the clubs last season.
Another "Original Six" showdown takes place at TD Garden, where the Boston Bruins host the New York Rangers at 8 p.m. ET. The Rangers won two of their three meetings with the Bruins in 2025-26, including a 6-2 triumph in Beantown.
The Yankees are -137 money line betting favorites against the Red Sox in the latest consensus MLB betting odds, while the Padres are -125 sports betting favorites against the Cubs. The Canadiens are -110 favorites over the Maple Leafs at sports betting apps, and the Rangers are -110 to win against the Bruins.
Below is a snapshot of what to watch and bet on Tuesday, Sept. 29. All times Eastern
MLB best bets, where to watch
Red Sox at Yankees
Time: 8 p.m. | Location: Bronx, N.Y. | TV: NBC | Stream: Fubo (Try for free)
SportsLine picks -- Model: Over 6 (-119) | Expert: Yankees ML (-133, Adam Thompson)
The Yankees and Red Sox combined for seven or more runs in only seven of their 13 regular-season meetings but did so in four of the six contests at Yankee Stadium. New York, which finished tied with the Minnesota Twins for second in the AL in runs with 739, produced at least nine in each of its last two games against Boston. The SportsLine Projection Model doesn't think the series opener will be a low-scoring one as the Over hits in almost 62% of its simulations. The Yankees went 4-2 at home against the Red Sox in the regular season, and Schlittler limited Boston to one run over 11 1/3 innings in his two starts in the Bronx. SportsLine expert Adam Thompson (45-23, +1644 on his last 68 MLB picks) likes the AL Cy Young favorite to continue that dominance and lead the Yankees to victory in Game 1.
Cubs at Padres
Time: 10 p.m. | Location: San Diego | TV: Peacock | Stream: Fubo (Try for free)
SportsLine picks -- Model: Over 7.5 (+100) | Expert: Fernando Tatis Jr. Over 1.5 total bases (+102, Angelo Magliocca)
The Cubs were the highest-scoring team in the major leagues this season, racking up 850 runs. The Padres were in the middle of the pack with 722 runs, but these clubs combined for at least nine in five of their six meetings in 2026. In addition, San Diego scored nine or more times in each of its final two regular-season contests. The SportsLine Projection Model sees the Cubs and Padres lighting up the scoreboard again as its simulations have the Over hitting almost 55% of the time. Fernando Tatis Jr. went 0-for-4 in his final regular-season game but collected at least two total bases in five of his previous six outings. SportsLine expert Angelo Magliocca is backing the Padres right fielder to have another solid performance at the plate in the series opener.
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NHL best bets, where to watch
Canadiens at Maple Leafs
Time: 7 p.m. | Location: Toronto | TV: ESPN+ | Stream: Fubo (Try for free)
SportsLine picks -- Model: Over 6.5 (-104) | Expert: Maple Leafs ML (-105, Jeff Hochman)
The Canadiens finished in the top 10 in the NHL in goals last season, ranking seventh with 279 tallies. They combined with the Maple Leafs for seven goals in their 2025-26 opener and matched that total in their second meeting of the campaign. Only two of Toronto's first 18 games last season had fewer than seven goals scored, and the SportsLine Projection Model believes the club will open 2026-27 with another high-scoring affair as the Over hits in more than 59% of its simulations, and it has assigned an "A" grade to the pick. Even though the Maple Leafs missed the playoffs for the first time in 10 years last season, SportsLine expert Jeff Hochman feels the Canadiens overachieved and is backing Toronto to skate away with the victory on Tuesday.
Rangers at Bruins
Time: 8 p.m. | Location: Boston | TV: ESPN | Stream: Fubo (Try for free)
SportsLine picks -- Model: Over 5.5 (-131) | Expert: Bruins -1 (+132, Matt Severance)
The Bruins were tied for 10th in the NHL last season with 268 goals, even though David Pastrnak failed to reach the 30-goal plateau for the first time in his last nine full campaigns. Boston and New York met three times in 2025-26, combining for seven or more goals on each occasion. A dozen goals were scored in their last meeting at TD Garden, and the SportsLine Projection Model thinks they'll light the lamp often on Tuesday as its simulations have the Over hitting more than 55% of the time. The Bruins won that aforementioned contest in Beantown 10-2, and SportsLine expert Matt Severance (9-2, +527 on his last 11 NHL spread picks) likes them to win by multiple goals again this time around.
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