| Show # | Air Date | Tape Date | Season | Type | Contestants | Comments |
|---|---|---|---|---|---|---|
| 5619 | 2009-01-29 | 2008-11-18 | 25 | Regular | Cynthia Astle, Brian Lee, Jack Feerick | |
| 5618 | 2009-01-28 | 2008-11-18 | 25 | Regular | Jack Feerick, Linda Tomsho, Andy Walvoord | |
| 5617 | 2009-01-27 | 2008-11-18 | 25 | Regular | Allison Jones, Andy Walvoord, Keith Costigan | Ask Alex #12: Travel. |
| 5616 | 2009-01-26 | 2008-11-18 | 25 | Regular | Melinda Hautala, Keith Costigan, Matt Kohlstedt | Matt Kohlstedt game 6. |
| 5615 | 2009-01-23 | 2008-11-12 | 25 | Regular | Quinn Conway, Rachel Kain, Matt Kohlstedt | Matt Kohlstedt game 5. |
| 5614 | 2009-01-22 | 2008-11-12 | 25 | Regular | Chris Schleicher, Luis Román, Matt Kohlstedt | Matt Kohlstedt game 4. |
| 5613 | 2009-01-21 | 2008-11-12 | 25 | Regular | Lynne McKenna Frazier, Trevor Janes, Matt Kohlstedt | Matt Kohlstedt game 3. |
| 5612 | 2009-01-20 | 2008-11-12 | 25 | Regular | Rebecca Wilkinson, Jerry Pyzansky, Matt Kohlstedt | Matt Kohlstedt game 2. |
| 5611 | 2009-01-19 | 2008-11-12 | 25 | Regular | Matt Kohlstedt, Lori Karman, Michele Lee Amundsen | Matt Kohlstedt game 1.First game in which reigning champion did not return. |
| 5610 | 2009-01-16 | 2008-11-11 | 25 | Regular | Priscilla Ball, Fayaz Kabani, Meagan Grote | |
| 5609 | 2009-01-15 | 2008-11-11 | 25 | Regular | Bill Menezes, Meagan Grote, Greg Jones | |
| 5608 | 2009-01-14 | 2008-11-11 | 25 | Regular | Judy Rowen, Greg Jones, Samantha Lubrani | |
| 5607 | 2009-01-13 | 2008-11-11 | 25 | Regular | Shawn St. Clair, Samantha Lubrani, Jack McPherson | Champion Update #2: Eddie Timanus. |
| 5606 | 2009-01-12 | 2008-11-11 | 25 | Regular | Pat Arnett, Debbie Israel, Jack McPherson | |
| 5605 | 2009-01-09 | 2008-11-05 | 25 | Regular | Ellen Gluckman, Jack McPherson, Kori Tyler | |
| 5604 | 2009-01-08 | 2008-11-05 | 25 | Regular | Erik Townsend, Kori Tyler, Ranjan Ramchandani | |
| 5603 | 2009-01-07 | 2008-11-05 | 25 | Regular | Rick Meneskie, Ranjan Ramchandani, Victoria Harkavy | |
| 5602 | 2009-01-06 | 2008-11-05 | 25 | Regular | Alison Miester, Ranjan Ramchandani, Victoria Harkavy | Ask Alex #11: Hobby. |
| 5601 | 2009-01-05 | 2008-11-05 | 25 | Regular | Andrew Kasson, Victoria Harkavy, Michael Portnoy | |
| 5600 | 2009-01-02 | 2008-11-04 | 25 | Regular | Rebecca Drinnon, Ben Reiter, Michael Portnoy | |
| 5599 | 2009-01-01 | 2008-11-04 | 25 | Regular | Edith Roberts, Michael Portnoy, Shyra Latiolais | |
| 5598 | 2008-12-31 | 2008-11-04 | 25 | Regular | Shyra Latiolais, Brian Gohacki, Scott Shive | Ask Alex #10: Friends. |
| 5597 | 2008-12-30 | 2008-11-04 | 25 | Regular | Emily Branson, Scott Shive, Jim Stevens | Jim Stevens game 7. |
| 5596 | 2008-12-29 | 2008-11-04 | 25 | Regular | Laura Mitchell, Ed Rozmiarek, Jim Stevens | Jim Stevens game 6. |
| 5595 | 2008-12-26 | 2008-10-21 | 25 | Regular | Mikey Stewart, Cathy Flanagan, Jim Stevens | Jim Stevens game 5. |
| 5594 | 2008-12-25 | 2008-10-21 | 25 | Regular | Deb DeGeorge, Lee Brooks, Jim Stevens | Jim Stevens game 4. |
| 5593 | 2008-12-24 | 2008-10-21 | 25 | Regular | Helene Glass, Marmi Maramot, Jim Stevens | Jim Stevens game 3.Ask Alex #9: Charities. |
| 5592 | 2008-12-23 | 2008-10-21 | 25 | Regular | Chet Perry, Sam Johnston, Jim Stevens | Jim Stevens game 2. |
| 5591 | 2008-12-22 | 2008-10-21 | 25 | Regular | Kristin Schleicher, Jim Stevens, Milt Hathaway | Jim Stevens game 1. |
| 5590 | 2008-12-19 | 2008-10-20 | 25 | Regular | Daniel Ogorzalek, Diane Hyra, Milt Hathaway | |
| 5589 | 2008-12-18 | 2008-10-20 | 25 | Regular | Milt Hathaway, Carrie Hotchkiss, Stevie Benson | |
| 5588 | 2008-12-17 | 2008-10-20 | 25 | Regular | Nicole Welch, Stevie Benson, George Yates | |
| 5587 | 2008-12-16 | 2008-10-20 | 25 | Regular | George Yates, Jeannie Leoutsakos, Justin Waters | Ask Alex #8: Languages. |
| 5586 | 2008-12-15 | 2008-10-20 | 25 | Regular | Justin Waters, Cyndy Hawley, Christine Carrino Gorowara | |
| 5585 | 2008-12-12 | 2008-10-15 | 25 | Regular | Tim Rask, Anthony Stinton, Christine Carrino Gorowara | |
| 5584 | 2008-12-11 | 2008-10-15 | 25 | Regular | Sean Kottke, Christine Carrino Gorowara, Matt Jacobs | Ask Alex #7: Clothes. |
| 5583 | 2008-12-10 | 2008-10-15 | 25 | Regular | Barb Schwartz, Matt Jacobs, Geoff Moore | |
| 5582 | 2008-12-09 | 2008-10-15 | 25 | Regular | Rich Smreker, Lydia Haile Fassett, Geoff Moore | |
| 5581 | 2008-12-08 | 2008-10-15 | 25 | Regular | Kathy Sahlmann, Geoff Moore, Ben Bishop | Ben Bishop game 5. |
| 5580 | 2008-12-05 | 2008-10-14 | 25 | Regular | Greg Morrison, Lauren Robb, Ben Bishop | Ben Bishop game 4. |
| 5579 | 2008-12-04 | 2008-10-14 | 25 | Regular | Michele Frankl, Ian Gould, Ben Bishop | Ben Bishop game 3.Ask Alex #6: Memory. |
| 5578 | 2008-12-03 | 2008-10-14 | 25 | Regular | Zac Showers, Josie Dickson, Ben Bishop | Ben Bishop game 2. |
| 5577 | 2008-12-02 | 2008-10-14 | 25 | Regular | Ben Bishop, Marcie Berson, Judy Mermelstein | Ben Bishop game 1.Champion Update #1: Frank Spangenberg. |
| 5576 | 2008-12-01 | 2008-10-14 | 25 | Regular | Michael Gerardi, Judy Mermelstein, Peter Pinnow | |
| 5575 | 2008-11-28 | 2008-09-26 | 25 | Regular | Kyle Holtan, Rose Pate, Peter Pinnow | |
| 5574 | 2008-11-27 | 2008-09-26 | 25 | Regular | Danielle Sexton, Peter Pinnow, Nathaniel Barnes | |
| 5573 | 2008-11-26 | 2008-09-26 | 25 | Regular | Erin Haramoto, Durant Gipson, Nathaniel Barnes | Ask Alex #5: Most money. |
| 5572 | 2008-11-25 | 2008-09-26 | 25 | Regular | Guil Prickette, Jillian Rebmann, Nathaniel Barnes | |
| 5571 | 2008-11-24 | 2008-09-26 | 25 | Regular | Jean MacKay Jackson, Nathaniel Barnes, Brian Muth | |
| 5560 | 2008-11-07 | 2008-09-24 | 25 | Regular | Martin Garnar, Lanny Springs, Brian Muth |