| № | # | Title | Directed by | Written by | Original air date | Production
code | U.S. viewers
(million) |
| 14 | 1 | "Chuck Versus the First Date" | Jason Ensler | Josh Schwartz & Chris Fedak | September 29, 2008 (NBC) | 3T7251 | 6.835 |
| 15 | 2 | "Chuck Versus the Seduction" | Allan Kroeker | Matthew Miller | October 6, 2008 (NBC) | 3T7252 | 5.832 |
| 16 | 3 | "Chuck Versus the Break-Up" | Robert Duncan McNeill | Scott Rosenbaum | October 13, 2008 (NBC) | 3T7253 | 6.172 |
| 17 | 4 | "Chuck Versus the Cougars" | Patrick Norris | Allison Adler | October 20, 2008 (NBC) | 3T7254 | 6.872 |
| 18 | 5 | "Chuck Versus Tom Sawyer" | Norman Buckley | Phil Klemmer | October 27, 2008 (NBC) | 3T7255 | 6.698 |
| 19 | 6 | "Chuck Versus the Ex" | Jay Chandrasekhar | Zev Borow | November 10, 2008 (NBC) | 3T7256 | 6.338 |
| 20 | 7 | "Chuck Versus the Fat Lady" | Jeffrey G. Hunt | Matthew Lau | November 17, 2008 (NBC) | 3T7257 | 6.889 |
| 21 | 8 | "Chuck Versus the Gravitron" | Allison Liddi-Brown | Chris Fedak | November 24, 2008 (NBC) | 3T7258 | 6.534 |
| 22 | 9 | "Chuck Versus the Sensei" | Jonas Pate | Anne Cofell Saunders | December 1, 2008 (NBC) | 3T7259 | 7.335 |
| 23 | 10 | "Chuck Versus the DeLorean" | Ken Whittingham | Matthew Miller | December 8, 2008 (NBC) | 3T7260 | 6.936 |
| 24 | 11 | "Chuck Versus Santa Claus" | Robert Duncan McNeill | Scott Rosenbaum | December 15, 2008 (NBC) | 3T7261 | 7.661 |
| 25 | 12 | "Chuck Versus the Third Dimension" | Robert Duncan McNeill | Chris Fedak | February 2, 2009 (NBC) | 3T7263 | 8.450 |
| 26 | 13 | "Chuck Versus the Suburbs" | Jay Chandrasekhar | Phil Klemmer | February 16, 2009 (NBC) | 3T7264 | 6.836 |
| 27 | 14 | "Chuck Versus the Best Friend" | Peter Lauer | Allison Adler | February 23, 2009 (NBC) | 3T7262 | 6.592 |
| 28 | 15 | "Chuck Versus the Beefcake" | Patrick Norris | Matthew Miller & Scott Rosenbaum | March 2, 2009 (NBC) | 3T7265 | 6.657 |
| 29 | 16 | "Chuck Versus the Lethal Weapon" | Allan Kroeker | Zev Borow & Matthew Lau | March 9, 2009 (NBC) | 3T7266 | 5.796 |
| 30 | 17 | "Chuck Versus the Predator" | Jeremiah Chechik | Chris Fedak | March 23, 2009 (NBC) | 3T7267 | 6.156 |
| 31 | 18 | "Chuck Versus the Broken Heart" | Kevin Bray | Allison Adler | March 30, 2009 (NBC) | 3T7268 | 5.723 |
| 32 | 19 | "Chuck Versus the Dream Job" | Robert Duncan McNeill | Phil Klemmer & Cory Nickerson | April 6, 2009 (NBC) | 3T7269 | 6.096 |
| 33 | 20 | "Chuck Versus the First Kill" | Norman Buckley | Scott Rosenbaum | April 13, 2009 (NBC) | 3T7270 | 6.212 |
| 34 | 21 | "Chuck Versus the Colonel" | Peter Lauer | Matthew Miller | April 20, 2009 (NBC) | 3T7271 | 6.113 |
| 35 | 22 | "Chuck Versus the Ring" | Robert Duncan McNeill | Chris Fedak & Allison Adler | April 27, 2009 (NBC) | 3T7272 | 6.199 |
