| ID | Interpret | Skladba | Album | |
| 61. | Toni Braxton | Un-Break My Heart | Virtual Dimension 514-678-4010 |    |
| 62. | Kane & Abel | He Will Break Your Heart | A Wall Of Soundalikes | |
| 63. | Toni Braxton | Un-Break My Heart | The World's Greatest Love Songs | |
| 64. | Toni Braxton | Un-Break My Heart | Secrets | |
| 65. | Toni Braxton | Un-Break My Heart | Secrets | |
| 66. | Toni Braxton | Un-Break My Heart | RTL Ultimative Chart Show | |
| 67. | Good Charlotte | Break Apart Her Heart | Good Morning Revival | |
| 68. | Good Charlotte | Break Apart Her Heart | Good Morning Revival | |
| 69. | Caitlin Cary & Thad Cockrell | Please Break My Heart | Begonias | |
| 70. | James Eric & Erin Vogel | I Am Trying To Break Your Heart | Jim and Erin Cover 'Yankee Hotel Foxtrot' Live | |
| 71. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 72. | Wilco | I am Trying to Break Your Heart | Yankee Hotel Foxtrot | |
| 73. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 74. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 75. | Michael Flowers | Break My Heart | Identified | |
| 76. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 77. | Faye Reis | Don't break my heart | Savage Rockin` Girls | |
| 78. | Wilco | I Am Trying to Break Your Heart | 06/13/09 - What Stage @ Bonnaroo, Manchester, TN - 16 | |
| 79. | The Beat Club | Don't Break My Heart | Paris | |
| 80. | Taio Cruz f. Ludacris | Break Your Heart | | |
| 81. | Wilco | I Am Trying To Break Your Heart (alt) | Yankee Hotel Foxtrot | |
| 82. | Caves | break your heart | Hail The Goer | |
| 83. | ATB | Break My Heart | Addicted To Music | |
| 84. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 85. | WILCO | i am trying to break your heart | Yankee Hotel Foxtrot | |
| 86. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 87. | Wilco | I Am Trying To Break Your Heart | Yankee Hotel Foxtrot | |
| 88. | Dave's True Story | How Do You Break a Heart? | Demo | |
| 89. | Yarn | Don't Break My Heart Again | Yarn | |
| 90. | Dave & Margaret Gloyd | Break My Heart | In This Place | |
