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| Date | Player | Team | Pos | Yrs | Amt | Opt | Ser | Agency |
|---|---|---|---|---|---|---|---|---|
| 04/14/2022 | Bryan Reynolds | PIT | CF | 2 | 13.500 | 0 | 2.163 | CAA Sports |
| 04/07/2022 | Ke'Bryan Hayes | PIT | 3B | 8 | 70.000 | 1 | 1.075 | Ballengee Group |
| 01/15/2018 | ⇑Felipe Vazquez | PIT | RP (Left-Handed) | 4 | 22.000 | 2 | 2.162 | Boras Corporation |
| 08/22/2016 | David Freese | PIT | 1B / 3B | 2 | 11.000 | 1 | 6.170 | CAA Sports |
| 05/17/2016 | Francisco Cervelli | PIT | C | 3 | 31.000 | 0 | 5.146 | Beverly Hills Sports Council |
| 04/03/2016 | Gregory Polanco | PIT | RF | 5 | 35.000 | 2 | 1.103 | Beverly Hills Sports Council |
| 01/19/2016 | Chris Stewart | PIT | C | 2 | 3.000 | 1 | 5.091 | James A. Kuzmich, PLLC |
| 04/08/2015 | Josh Harrison | PIT | 2B / 3B | 3 | 24.500 | 2 | 3.033 | MSM Sports Management |
| 03/26/2014 | Starling Marte | PIT | LF | 6 | 31.000 | 2 | 1.070 | Legacy Agency |
| 12/11/2013 | Charlie Morton | PIT | SP | 3 | 21.000 | 1 | 5.010 | Jet Sports Management |
| 03/04/2012 | Andrew McCutchen | PIT | CF | 6 | 51.500 | 1 | 2.123 | Aegis Sports Management |
| 08/19/2011 | Jose Tabata | PIT | LF | 6 | 15.000 | 3 | 1.086 | ACES |
| 02/17/2009 | Nate McLouth | PIT | CF | 3 | 15.750 | 1 | 3.056 | The Sparta Group |
| 01/30/2009 | Paul Maholm | PIT | SP | 3 | 14.500 | 1 | 3.037 | Bo McKinnis |
| 12/28/2008 | Ryan Doumit | PIT | C | 3 | 11.500 | 2 | 3.120 | Apex Baseball |
| 04/03/2008 | Matt Capps | PIT | RP (Closer) | 2 | 3.050 | 0 | 2.026 | Wasserman |
| 03/16/2008 | Ian Snell | PIT | SP | 3 | 8.600 | 2 | 2.088 | Joe Sroba |
| 02/05/2008 | Freddy Sanchez | PIT | 2B | 2 | 11.000 | 1 | 4.052 | Apex Baseball |
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