| Date/Season | Transaction |
|---|
| 9/11/2020 | Pittsburgh Penguins send Yakov Trenin, Spencer Watson, Adam Janosik, PIT 2028 Rnd 2 to the Chicago Blackhawks for Dominik Masin, Jacob de la Rose, $1,000,000 |
| 4/23/2020 | Pittsburgh Penguins send Patrik Laine to the Detroit Red Wings for Samuel Girard, Yakov Trenin, Julien Gauthier, OTT 2025 Rnd 1 , SJS 2025 Rnd 1 |
| 2/17/2020 | Toronto Maple Leafs send Yakov Trenin, Kent Patterson, MON 2025 Rnd 2 to the Detroit Red Wings for Lukas Kaspar, Carson Soucy |
| 3/29/2019 | Toronto Maple Leafs send Eric Staal to the Edmonton Oilers for Trevor Lewis, Yakov Trenin |
| 2021 | Drafted in the 2nd round, 57th overall by Edmonton (from Pittsburgh) |
