| # | Wrestler Name | Date |
| 1 | B. Cool | 12/31/2007 |
| 2 | B. Cool | 01/27/2008 |
| 3 | B. Cool | 02/01/2008 |
| 4 | Joe Kerr | 02/24/2008 |
| 5 | Alan Drake | 03/30/2008 |
| 6 | Alan Drake | 04/11/2008 |
| 7 | Alan Drake | 04/18/2008 |
| 8 | Alan Drake | 06/29/2008 |
| 9 | Alan Drake | 07/27/2008 |
| 10 | VACATED | 09/22/2008 |
| 11 | Larell | 10/31/2008 |
| 12 | Larell | 01/02/2009 |
| 13 | Larell | 02/22/2009 |
| 14 | VACATED | 02/22/2009 |
| 15 | Larell | 04/17/2009 |
| 16 | Tsuyoshi Dai | 04/26/2009 |
| 17 | Jac Morgan | 05/31/2009 |
| 18 | Simon Kayne | 06/19/2009 |
| 19 | Samantha Lavelle | 07/26/2009 |
| 20 | Brian Sasso | 08/14/2009 |
| 21 | Brian Sasso | 09/21/2009 |
Details
| 1 | B. Cool won the 8 man elimination chamber at New Year's Evolution. Was only seven competitors as Aquiro no showed. |
| 2 | At Turbulence, Razor passed out due to the Cool Clutch and the referee stopped the match. |
| 3 | B. Cool defeated Dr. Ironfist in a Rock Paper Scissors match at Edge. |
| 4 | Joe Kerr defeated B. Cool by pinfall at February Revolution. |
| 5 | Alan Drake defeated Joe Kerr at Bloodsport by breaking his leg in a Sticks & Stones Match. |
| 6 | Alan defeated B. Cool in an Ironman Match at Edge. |
| 7 | Alan Drake defeated Glacier at Edge by pinfall. |
| 8 | Alan Drake defeated Lord Victor Haddon at Invasion. As per stipulation for that match, Haddon's name has been stricken from the Skyfall Championship history. |
| 9 | Alan Drake defeated James Lightening by pinfall at Infected. |
| 10 | Alan Drake vacated the title before his match with Nick Saber at Fallout. |
| 11 | Larell won the 2008 Costume Battle Royal at Trick or Treat. |
| 12 | Larell defeated Lich by pinfall at Edge. |
| 13 | Larell defeated Shane Evans and Roach at February Revolution. He pinned Roach for the win. |
| 14 | All titles were vacated by Reynolds at February Revolution. |
| 15 | Kyra Pierce reinstated the Skyfall title and gave it to the last champion. |
| 16 | Tsuyoshi Dai defeated Larell by pinfall at Altitude. |
| 17 | Jac Morgan defeated Tsuyoshi Dai by submission at Maelstrom. |
| 18 | Simon Kayne defeated Jac Morgan by pinfall at Edge. |
| 19 | Samantha defeated Simon Kayne by pinfall at Infected. Sirus Shade placed a 24/7 rule on the title. |
| 20 | Brian Sasso attacked Sam Lavelle after the Stephanie Frost vs. Fire & Ice match at Edge. |
| 21 | Brian Sasso retained against Sirus Shade by pinfall at Fallout. |