| Date | Time | Headline |
|---|
| Sat May 18 | 13:24 | Drew Smyly Starting Rehab Assignment Next Week |
| Tue May 7 | 19:23 | Drew Smyly, Jordan Wicks Throwing Bullpens Tuesday |
| Fri May 3 | 12:26 | Jordan Wicks, Drew Smyly Playing Catch |
| Tue Apr 23 | 17:22 | Kyle Hendricks, Drew Smyly Placed On Injured List |
| Sun Feb 4 | 22:16 | Javier Assad, Drew Smyly, Hayden Wesneski In Mix For No. 5 Role |
| Mon Nov 6 2023 | 21:10 | Drew Smyly Returning To Cubs Next Season |
| Sun Aug 20 2023 | 19:39 | Drew Smyly To Rejoin Rotation On Tuesday |
| Wed Aug 16 2023 | 18:11 | Drew Smyly Expected To Rejoin Starting Rotation |
| Mon Jul 31 2023 | 14:11 | Drew Smyly Returning To Rotation Wednesday |
| Sat Jul 22 2023 | 12:39 | Drew Smyly Available Out Of Bullpen Saturday |
| Thu May 18 2023 | 00:15 | Drew Smyly Works Six Strong Innings Against Astros |
| Mon May 1 2023 | 22:11 | Drew Smyly Goes Seven Strong Innings In Victory |
| Fri Apr 21 2023 | 19:53 | Drew Smyly Takes Perfect Game Into The Eighth On Friday |
| Sat Mar 25 2023 | 10:24 | Drew Smyly Fine-Tuning His Mechanics |
| Thu Dec 22 2022 | 19:15 | Drew Smyly In Agreement With The Cubs |
| Sun Dec 18 2022 | 13:19 | Cubs, Drew Smyly Close To A Deal |
| Wed Nov 9 2022 | 00:15 | Drew Smyly Declines Option, Considering Cubs Reunion |
| Fri Sep 30 2022 | 14:02 | Drew Smyly To Start Saturday |
| Thu Sep 15 2022 | 11:45 | Drew Smyly Picks Up His Seventh Win Wednesdasy |
| Fri Aug 12 2022 | 00:12 | Drew Smyly Strikes Out Nine In Win |
