| Date/Season | Transaction |
|---|---|
| 4/21/2024 | Philadelphia Flyers send Emile Poirier to the San Jose Sharks for Drake Caggiula, Nick Bonino |
| 1/28/2023 | Boston Bruins send Rickard Rakell, Thomas Wilson, Zach Redmond, Drake Caggiula to the San Jose Sharks for Stefan Noesen (rental), Sven Baertschi, John Erskine, Alexander Perevalov |
| 10/8/2020 | Vancouver Canucks send Drake Caggiula to the Boston Bruins for Jeremy Bracco |
| 2023 | Drafted in the 3rd round, 79th overall by Calgary (from NYRangers) |
