The Most Exciting and Heartbreaking Regular Season Finishes in Blue Jays History

For most of the franchise's existence, the Toronto Blue Jays have either comfortably qualified for the playoffs or fallen out of contention before the final week. But every so often, their season has come down to the final days, final innings and sometimes even a final out.

Some of those endings remain among the most thrilling moments in franchise history. Others still sting. From the epic collapse of 1987 to the playoff races of recent years, these are the regular season finishes that generated the most excitement and heartbreak before October ever began.

1. 1987: The Collapse That Defined a Generation

With just seven games remaining, Toronto owned a 3.5-game lead over the Detroit Tigers and had already accumulated 96 victories. The division title seemed all but secured.

Instead, the unthinkable happened. The Blue Jays lost seven consecutive games.

The season's final game on Oct. 4 remains burned into the memory of many Canadian baseball fans.

Jimmy Key was brilliant, allowing only three hits. Unfortunately, one of them was a Larry Herndon solo home run in the second inning. Detroit won 1-0, captured the division and sent Toronto home.

The Blue Jays finished 96-66. No wild cards back then. No playoffs.

2. 2015: The Week That Ended a 22-Year Drought

Technically, the Blue Jays had already clinched before the final day of the season. Yet, no discussion of dramatic regular season finishes is complete without mentioning one of the most exciting stretch runs in franchise history.

Toronto entered August looking like a playoff hopeful.

The additions of David Price, Troy Tulowitzki, Ben Revere and LaTroy Hawkins transformed the roster. Combined with an explosive offence featuring Josh Donaldson, José Bautista and Edwin Encarnación, the club surged past the Yankees in one of the most memorable pennant chases in team history.

When the Jays finally clinched the AL East on Sept. 30, it ended a 22-year postseason drought.

3. 1989: Winning the East on the Final Weekend

The 1989 Blue Jays authored one of the most exciting September drives in franchise history.

Toronto spent much of the season chasing Baltimore before surging late. The division race remained tight into the final weekend, creating palpable tension throughout the city.

The Jays ultimately overtook the Orioles and secured the American League East crown.

The finishing stretch seemed to prove to both the roster and its fans that lessons had been learned from the heartbreak of 1987. Two years after collapsing down the stretch, Toronto delivered.

4. 2016: Clinching in Boston and Setting Up October Magic

If 1987 was the franchise's greatest regular-season heartbreak, 2016 stands among its most satisfying finishes.

One year after José Bautista's unforgettable bat flip season, the Blue Jays again found themselves locked in a tight postseason race entering the final week. The pressure mounted as Toronto stumbled, losing four of five games at a critical moment.

They entered the final day of the season in Boston knowing they needed one more win to lock down home-field advantage for the American League Wild Card Game.

Aaron Sanchez took the mound and delivered one of the best starts of his career.

Troy Tulowitzki broke up a scoreless tie with a go-ahead RBI single in the eighth inning. Roberto Osuna earned the save, securing a 2-1 victory.

The importance of the win wasn't fully appreciated until two days later.

Because Toronto earned home-field advantage, the Wild Card showdown against Baltimore was played at Rogers Centre rather than Camden Yards.

That game produced Edwin Encarnación's legendary extra-inning walk-off home run, one of the defining moments in franchise history.

5. 2021: Ninety-One Wins and Nothing To Show for It

Playing much of the season away from Toronto because of pandemic-related restrictions, the Blue Jays still finished with a 91-71 record. Vladimir Guerrero Jr. nearly won the Triple Crown. Robbie Ray captured the Cy Young Award. Marcus Semien set a record for home runs by a second baseman.

Entering the final weekend, four AL East teams remained in the playoff race. The Blue Jays needed virtually everything to go right.

The Jays did their part, but the Yankees and Red Sox kept winning.

Toronto missed the postseason by a single game despite recording 91 victories, the highest win total ever by a Blue Jays team that failed to qualify for the playoffs.

With a strong September, the Jays repeatedly put themselves back into contention. Yet the hole dug earlier in the season proved too deep.

6. 1990: So Close, Yet Not Quite

The 1990 season shared more than a few similarities with 1987.

The Blue Jays entered the season's final day still alive in the American League East race. The path was difficult but possible. Toronto needed help and needed to win.

While the Blue Jays battled the Baltimore Orioles, the Boston Red Sox defeated the Chicago White Sox to secure the division title. Minutes later, Toronto's own game slipped away when closer Tom Henke surrendered a ninth-inning home run.

The loss punctuated a frustrating finish in which Toronto dropped six of its final eight games. A crucial late-season series against Boston had already shifted momentum, giving the Red Sox an opening.

7. 1985: The Original Breakthrough

After unsuccessfully chasing the Tigers in 1984, the Blue Jays spent 1985 battling for first place from Opening Day onward. They nearly relinquished the division title down the stretch to a surging Yankees squad.

On Oct. 6, 1985, Toronto defeated the Yankees at Exhibition Stadium to secure the franchise's first division title, completing a remarkable journey from expansion club to legitimate contender.

8. 2023: Sneaking Into October

The 2023 season ended with relief more than celebration.

Toronto entered its final series against the Tampa Bay Rays needing one final push to lock down an American League Wild Card berth. The opportunity was there to clinch on the field, but the Blue Jays stumbled at the finish line. A 7-5 loss to the Rays on Sept. 29 left their postseason status unresolved and forced players, coaches and fans to turn their attention to the out-of-town scoreboard.

The next day, Toronto officially secured a playoff spot thanks to help from the Arizona Diamondbacks, who defeated the Houston Astros.

The Blue Jays reached October for the third time in four years, but the accomplishment felt more like survival than triumph.

9. 1998: The End of an Era

Not every memorable ending involves a playoff berth or a dramatic collapse.

The 1998 season marked the final chapter of the Blue Jays' championship era. Just five years removed from winning back-to-back World Series titles, the Jays remained mathematically alive late into September but could never truly gain ground.

When the season ended with an 88-74 record, Toronto finished third behind New York and Boston. In most divisions, that record would have made for a compelling race. In the AL East, it left the Jays watching from home.

Over 50 years, the Blue Jays have experienced nearly every kind of regular season ending imaginable. They have celebrated division titles, ended historic droughts and punched tickets to October in dramatic fashion. They have also endured crushing collapses, near misses and seasons that unravelled.

By the end of this month, the franchise will have another season to reflect upon. One that started with such promise, felt like it was slipping away and culminated with… Well, we’ll have to see whether or not 2026 makes this list next year.