The Yankees have had 1st-place finish droughts before: 1903-20, 1965-75, and 1982-95 (or 1982-93 if you count the Strike year of 1994). But 7 years between the 2012 title and this year's was too much, given their resources.
For this list, I am counting, even if Major League Baseball does not do so officially:
* Pennants in the single-division Leagues prior to 1969.
* The split-season Divisional Champions of 1981.
* The teams that had the best overall record in each Division in 1981, even if they didn't make the Playoffs under the format in place that year.
* The teams that were in first place when the Strike of 1994 hit.
* The teams that lost Playoffs for the Pennant in the single-division era (1901-1968).
It does not, however, count Pennants won as Wild Card entries.
All ties in this ranking are broken by most recent finish. This season's Division winners in bold.
1. New York Yankees, 49: 1921, '22, '23, '26, '27, '28, '32, '36, '37, '38, '39, '41, '42, '43, '47, '49, '50, '51, '52, '53, '55, '56, '57, '58, '60, '61, '62, '63, '64, '76, '77, '78, '80, '81 (1st-half and overall winners), '94 (led when strike hit), '96, '98, '99, 2000, '01, '02, '03, '04, '05, '06, '09, '11, '12, '19.
2. St. Louis Cardinals, 31: 1885, '86, '87, '88, 1926, '28, '30, '31, '34, '42, '43, '44, '46, '64, '67, '68, '81 (aggregate winners but didn't lead in either half), '82, '85, '87, '96, 2000, '01, '02, '04, '05, '06, '09, '13, '14, '15, '19.
3. Los Angeles Dodgers, 25: 1959, '62, '63, '65, '66, '74, '77, '78, '80, '81 (1st-half and overall winners), '83, '85, '88, '94 (led when strike hit), '95, 2004, '08, '09, '13, '14, '15, '16, '17, '18, '19. Previously reached as Brooklyn Dodgers in 1889, '90, '99, 1900, '16, '20, '41, '46, '47, '49, '51, '52, '53, '55 and '56 -- total, 39.
4. Chicago Cubs, 23: 1876, '80, '81, '82, '85, '86, 1906, '07, '08, '10, '18, '29, '32, '35, '38, '45, '84, '89, 2003, '07, '08, '16, '17.
5. Boston Red Sox, 20: 1903, '04, '12, '15, '16, '18, '46, '48, '67, '75, '78, '86, '88, '90, '95, 2007, '13, '16, '17, '18.
6. Atlanta Braves, 19: 1969, '82, '91, '92, '93, '95, '96, '97, '98, '99, 2000, '01, '02, '03, '04, '05, '13, '18, '19. Previously reached as Boston Braves in 1877, '78, '83, '91, '92, '93, '97, '98, 1914 and '48; and as Milwaukee Braves in 1957, '58 and '59 -- total, 32.
7. Cincinnati Reds, 18: 1882, 1919, '39, '40, '61, 1970, '72, '73, '75, '76, '79, '81 (aggregate winners but didn't lead in either half), '90, '94 (led when strike hit), '95, 2010, '12, '13.
8. Pittsburgh Pirates, 16: 1901, '02, '03, '09, '25, '27, '60, '70, '71, '72, '74, '75, '79, '90, '91, '92.
9. Oakland Athletics, 16: 1971, '72, '73, '74, '75, '81 (1st-half and overall winners), '88, '89, '90, '92, 2000, '02, '03, '06, '12, '13. Previously reached as Philadelphia Athletics in 1902, '05, '10, '11, '13, '14, '29, '30 and '31 -- total, 25.
10. Detroit Tigers, 15: 1907, '08, '09, '34, '35, '40, '45, '68, '72, '84, '87, 2011, '12, '13, '14.
11. Philadelphia Phillies, 14: 1915, '50, '76, '77, '78, '80, '81 (1st-half), '83, '93, 2007, '08, '09, '10, '11.
12. Cleveland Indians, 13: 1920, '48, '54, '95, '96, '97, '98, '99, 2001, '07, '16, '17, '18.
13. Minnesota Twins, 12: 1965, '69, '70, '87, '91, 2002, '03, '04, '06, '09, '10, '19. Previously reached as Washington Senators in 1924, '25 and '33 -- total, 15.
18. Kansas City Royals, 9: 1976, '77, '78, '80, '81 (2nd-half winners), '84, '85, 2014, '15.
19. Los Angeles Angels, 9: 1979, '82, '86, '95, 2004, '05, '07, '08, '09, '14.
20. Texas Rangers, 8: 1994 (led when strike hit), '96, '98, '99, 2010, '11, '15, '16.
21. Toronto Blue Jays, 6: 1985, '89, '91, '92, '93, 2015.
22. New York Mets, 6: 1969, '73, '86, '88, 2006, '15.
23. San Diego Padres, 6: 1984, '96, '98, 2005, '06, '07.
24. Arizona Diamondbacks, 5: 1999, 2001, '02, '07, '11.
25. Milwaukee Brewers, 4: 1981 (2nd-half winners), '82, 2011, '18.
26. Washington Nationals, 4: 2012, '14, '16, '17. Also won NL East as Montreal Expos in 1981 (2nd-half and overall winners) and '94 (led when strike hit) -- total, 5.
27. Seattle Mariners, 3: 1995, '97, 2001.
28. Tampa Bay Rays, 2: 2008, '11.
29. Colorado Rockies, 0: 4 Playoff appearances, all via the Wild Card.
30. Miami Marlins, 0: 2 Playoff appearances, both via the Wild Card.
Leading their respective Divisions are: In the American League, the Yankees, Detroit and Oakland; in the National League, Atlanta, St. Louis and Los Angeles.
Last Division Title by Each Team:
1. New York Yankees, 2019
2. Los Angeles Dodgers, 2019
3. Houston Astros, 2019
4. Atlanta Braves, 2019
5. St. Louis Cardinals, 2019
6. Minnesota Twins, 2019
7. Boston Red Sox, 2018
8. Cleveland Indians, 2018
9. Milwaukee Brewers, 2018
10. Chicago Cubs, 2017
11. Washington Nationals, 2017
12. Texas Rangers, 2016
13. Kansas City Royals, 2015
14. Toronto Blue Jays, 2015
15. New York Mets, 2015
16. Detroit Tigers, 2014
17. Baltimore Orioles, 2014
18. Los Angeles Angels, 2014
19. Cincinnati Reds, 2013
20. Oakland Athletics, 2013
21. San Francisco Giants, 2012
22. Philadelphia Phillies, 2011
23. Arizona Diamondbacks, 2011
24. Tampa Bay Rays, 2011
25. Chicago White Sox, 2008
26. San Diego Padres, 2007
27. Seattle Mariners, 2001
28. Pittsburgh Pirates, 1992
29. Colorado Rockies, none
30. Miami Marlins, none
For this list, I am counting, even if Major League Baseball does not do so officially:
* Pennants in the single-division Leagues prior to 1969.
* The split-season Divisional Champions of 1981.
* The teams that had the best overall record in each Division in 1981, even if they didn't make the Playoffs under the format in place that year.
* The teams that were in first place when the Strike of 1994 hit.
* The teams that lost Playoffs for the Pennant in the single-division era (1901-1968).
It does not, however, count Pennants won as Wild Card entries.
All ties in this ranking are broken by most recent finish. This season's Division winners in bold.
1. New York Yankees, 49: 1921, '22, '23, '26, '27, '28, '32, '36, '37, '38, '39, '41, '42, '43, '47, '49, '50, '51, '52, '53, '55, '56, '57, '58, '60, '61, '62, '63, '64, '76, '77, '78, '80, '81 (1st-half and overall winners), '94 (led when strike hit), '96, '98, '99, 2000, '01, '02, '03, '04, '05, '06, '09, '11, '12, '19.
2. St. Louis Cardinals, 31: 1885, '86, '87, '88, 1926, '28, '30, '31, '34, '42, '43, '44, '46, '64, '67, '68, '81 (aggregate winners but didn't lead in either half), '82, '85, '87, '96, 2000, '01, '02, '04, '05, '06, '09, '13, '14, '15, '19.
3. Los Angeles Dodgers, 25: 1959, '62, '63, '65, '66, '74, '77, '78, '80, '81 (1st-half and overall winners), '83, '85, '88, '94 (led when strike hit), '95, 2004, '08, '09, '13, '14, '15, '16, '17, '18, '19. Previously reached as Brooklyn Dodgers in 1889, '90, '99, 1900, '16, '20, '41, '46, '47, '49, '51, '52, '53, '55 and '56 -- total, 39.
4. Chicago Cubs, 23: 1876, '80, '81, '82, '85, '86, 1906, '07, '08, '10, '18, '29, '32, '35, '38, '45, '84, '89, 2003, '07, '08, '16, '17.
5. Boston Red Sox, 20: 1903, '04, '12, '15, '16, '18, '46, '48, '67, '75, '78, '86, '88, '90, '95, 2007, '13, '16, '17, '18.
6. Atlanta Braves, 19: 1969, '82, '91, '92, '93, '95, '96, '97, '98, '99, 2000, '01, '02, '03, '04, '05, '13, '18, '19. Previously reached as Boston Braves in 1877, '78, '83, '91, '92, '93, '97, '98, 1914 and '48; and as Milwaukee Braves in 1957, '58 and '59 -- total, 32.
7. Cincinnati Reds, 18: 1882, 1919, '39, '40, '61, 1970, '72, '73, '75, '76, '79, '81 (aggregate winners but didn't lead in either half), '90, '94 (led when strike hit), '95, 2010, '12, '13.
9. Oakland Athletics, 16: 1971, '72, '73, '74, '75, '81 (1st-half and overall winners), '88, '89, '90, '92, 2000, '02, '03, '06, '12, '13. Previously reached as Philadelphia Athletics in 1902, '05, '10, '11, '13, '14, '29, '30 and '31 -- total, 25.
10. Detroit Tigers, 15: 1907, '08, '09, '34, '35, '40, '45, '68, '72, '84, '87, 2011, '12, '13, '14.
11. Philadelphia Phillies, 14: 1915, '50, '76, '77, '78, '80, '81 (1st-half), '83, '93, 2007, '08, '09, '10, '11.
12. Cleveland Indians, 13: 1920, '48, '54, '95, '96, '97, '98, '99, 2001, '07, '16, '17, '18.
13. Minnesota Twins, 12: 1965, '69, '70, '87, '91, 2002, '03, '04, '06, '09, '10, '19. Previously reached as Washington Senators in 1924, '25 and '33 -- total, 15.
14. Chicago White Sox, 11: 1901, '06, '17, '19, '59, '83, '93, '94 (led when strike hit), 2000, '05, '08.
15. Houston Astros, 10: 1980, '81 (2nd-half winners), '86, '97, '98, '99, 2001, '17, '18, '19.
16. Baltimore Orioles, 10: 1966, '69, '70, '71, '73, '74, '79, '83, '97, 2014. Previously reached as St. Louis Browns in 1944, for a total of 11.
17. San Francisco Giants, 9: 1962, '71, '87, '89, '97, 2000, '03, '10, '12. Previously reached as New York Giants in 1888, '89, 1904, '05, '08, '11, '12, '13, '17, '21, '22, '23, '24, '33, '36, '37, '51 and '54 -- total, 26.
15. Houston Astros, 10: 1980, '81 (2nd-half winners), '86, '97, '98, '99, 2001, '17, '18, '19.
16. Baltimore Orioles, 10: 1966, '69, '70, '71, '73, '74, '79, '83, '97, 2014. Previously reached as St. Louis Browns in 1944, for a total of 11.
17. San Francisco Giants, 9: 1962, '71, '87, '89, '97, 2000, '03, '10, '12. Previously reached as New York Giants in 1888, '89, 1904, '05, '08, '11, '12, '13, '17, '21, '22, '23, '24, '33, '36, '37, '51 and '54 -- total, 26.
18. Kansas City Royals, 9: 1976, '77, '78, '80, '81 (2nd-half winners), '84, '85, 2014, '15.
19. Los Angeles Angels, 9: 1979, '82, '86, '95, 2004, '05, '07, '08, '09, '14.
20. Texas Rangers, 8: 1994 (led when strike hit), '96, '98, '99, 2010, '11, '15, '16.
21. Toronto Blue Jays, 6: 1985, '89, '91, '92, '93, 2015.
22. New York Mets, 6: 1969, '73, '86, '88, 2006, '15.
24. Arizona Diamondbacks, 5: 1999, 2001, '02, '07, '11.
25. Milwaukee Brewers, 4: 1981 (2nd-half winners), '82, 2011, '18.
26. Washington Nationals, 4: 2012, '14, '16, '17. Also won NL East as Montreal Expos in 1981 (2nd-half and overall winners) and '94 (led when strike hit) -- total, 5.
27. Seattle Mariners, 3: 1995, '97, 2001.
28. Tampa Bay Rays, 2: 2008, '11.
29. Colorado Rockies, 0: 4 Playoff appearances, all via the Wild Card.
30. Miami Marlins, 0: 2 Playoff appearances, both via the Wild Card.
Leading their respective Divisions are: In the American League, the Yankees, Detroit and Oakland; in the National League, Atlanta, St. Louis and Los Angeles.
Last Division Title by Each Team:
1. New York Yankees, 2019
2. Los Angeles Dodgers, 2019
3. Houston Astros, 2019
4. Atlanta Braves, 2019
5. St. Louis Cardinals, 2019
6. Minnesota Twins, 2019
7. Boston Red Sox, 2018
8. Cleveland Indians, 2018
9. Milwaukee Brewers, 2018
10. Chicago Cubs, 2017
11. Washington Nationals, 2017
12. Texas Rangers, 2016
13. Kansas City Royals, 2015
14. Toronto Blue Jays, 2015
15. New York Mets, 2015
16. Detroit Tigers, 2014
17. Baltimore Orioles, 2014
18. Los Angeles Angels, 2014
19. Cincinnati Reds, 2013
20. Oakland Athletics, 2013
21. San Francisco Giants, 2012
22. Philadelphia Phillies, 2011
23. Arizona Diamondbacks, 2011
24. Tampa Bay Rays, 2011
25. Chicago White Sox, 2008
26. San Diego Padres, 2007
27. Seattle Mariners, 2001
28. Pittsburgh Pirates, 1992
29. Colorado Rockies, none
30. Miami Marlins, none