| ID | Interpret | Skladba | Album | |
| 61. | Sphere of Hip-Hop | Guess Who | |  |
| 62. | Cuff The Duke | I Guess It's Up To You | The Grad Club, Kingston, 23 February 2007 | |
| 63. | Grand Theft Bus | I Guess Not I Guess | Made Upwards |  |
| 64. | Too Hip For The Room | I Guess I'll Be OK | What Am I Doing On The Moon? | |
| 65. | Cuff The Duke | I Guess It's Up To You | The Grad Club, Kingston, 23 February 2007 | |
| 66. | Blaque Unit | I Guess | Smack That EP | |
| 67. | Bhale BaCce Sound - sound system reggae ragga hip hop | Guess | Les enfants gentils cd.2 | |
| 68. | Alejandra & Aeron | End I Guess, | Bousha Blue Blazes | |
| 69. | Jonna Gault and Her Symphonopop Scene | Wonder Why, I Guess | More Phonoanomalies for Hi-Fi Bugs | |
| 70. | Colleen AF Venable and Annie Sanders | Guess Who | Fluff Radio Review 2006 Sampler | |
| 71. | Mykal Rose ls. Danny Scrilla | Guess Who | | |
| 72. | Dave's True Story | Who Would Guess? | Nature Preview | |
| 73. | Barbara Jean English | Guess Who | | |
| 74. | Too Hip For The Room | I Guess I'll Be OK | What Am I Doing On The Moon? | |
| 75. | Too Hip For The Room | I Guess I'll Be OK | What Am I Doing On The Moon? | |
| 76. | Phil Graham Band | Guess Who | Al's Casino | |
| 77. | SYLEENA JOHNSON | GUESS WHAT | GUESS WHAT |  |
| 78. | 93X HALF-ASSED MORNING SHOW | Who Guess Who | BITS | |
| 79. | Ryan Montbleau Band | My Best Guess | Ryan Montbleau 2-10-2009 Honest FM | |
| 80. | B33J | 'guess' | Yet To Be | |
| 81. | Get Help | I'd Guess, But You Know | Reminders | |
| 82. | bobsadviceforstocks | Guess? (GES) | Stock Picks Bob's Advice | |
| 83. | The Blood Orange | I Guess You Can't | The Blood Orange EP | |
| 84. | Fatty | Guess Ho? | Music from Shock&Awkward | |
| 85. | Slick Shoes | I Guess | | |
| 86. | Aizel | I Guess We Been Who We Are | Ice Steps | |
| 87. | Aizel | I Guess We Been Who We Are | Ice Steps | |
| 88. | Drew Gardner | So I Guess | Segue Series, Bowery Poetry Club, New York City, October 18, 2008 | |
| 89. | Coarts | Guess I Know | Coarts - Pictures LP | |
| 90. | Slick Shoes | I Guess | | |
