| ID | Interpret | Skladba | Album | |
| 31. | All Time Low | Break Your Little Heart | Nothing Personal |   |
| 32. | Good Charlotte | Break Apart Her Heart | Good Morning Revival |  |
| 33. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 34. | Dave & Margaret Gloyd | Break My Heart | In This Place | |
| 35. | Good Charlotte | Break Apart Her Heart | Good Morning Revival | |
| 36. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 37. | Westlife | How to Break a Heart | Where We Are | |
| 38. | Hilary Duff | Break My Heart | Most Wanted | |
| 39. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 40. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 41. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 42. | Taio Cruz f. Ludacris | Break Your Heart | | |
| 43. | Wilco | I Am Trying To Break Your Heart (alt) | Yankee Hotel Foxtrot | |
| 44. | Robert Jardell | You'll Never Break My Heart | Robert Jardell and Pure Cajun | |
| 45. | James Eric & Erin Vogel | I Am Trying To Break Your Heart | Jim and Erin Cover 'Yankee Hotel Foxtrot' Live | |
| 46. | Cry Baby | Heart Break | V/A PALLADIUM - ROCK GENEVE 81 EN PUBLIC Comp LP | |
| 47. | Cry Baby | Heart Break | V/A PALLADIUM - ROCK GENEVE 81 EN PUBLIC Comp LP | |
| 48. | Carrie Newcomer | Not Going To Let You Break My Heart | | |
| 49. | Carrie Newcomer | Not Going To Let You Break My Heart | | |
| 50. | WILCO | i am trying to break your heart | Yankee Hotel Foxtrot | |
| 51. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 52. | Wilco | I Am Trying to Break Your Heart | 06/13/09 - What Stage @ Bonnaroo, Manchester, TN - 16 | |
| 53. | Brookville | Break My Heart | Broken Lights | |
| 54. | BLOOM | Don't Break This Heart | the ModPopPunk Archives | |
| 55. | Dave's True Story | How Do You Break a Heart? | Demo | |
| 56. | A.D. | Heart break | Records | |
| 57. | A.D. | Heart break | Records | |
| 58. | Michael Flowers | Break My Heart | Identified | |
| 59. | Mayor Byrne | Break My Heart | Meander. | |
| 60. | Taio Cruz | Break Your Heart | | |
