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| 2021 | |
|---|---|
| 11/05/2021 | Filed for free agency. |
| 11/05/2021 | Outrighted to Durham (AAA). |
| 11/05/2021 | Missed all 162 regular season and all 4 playoff games (right flexor strain). |
| 2/22/2021 | Right flexor strain, 60-day injured list. |
| 2/17/2021 | Re-signed as a free agent by the Tampa Bay Rays to a one-year contract. |
| 2020 | |
| 10/14/2020 | Refused minor league assignment from the Tampa Bay Rays and opted for free agency. |
| 10/11/2020 | Designated for assignment by the Tampa Bay Rays. |
| 10/11/2020 | Missed the last 2 playoff games (right flexor strain). |
| 10/08/2020 | Removed from the Tampa Bay Rays playoff roster. |
| 10/08/2020 | Right flexor strain, 10-day injured list. |
| 9/15/2020 | Missed 32 games (right biceps tendinitis). |
| 8/09/2020 | Right biceps tendinitis, 10-day injured list. |
| 1/10/2020 | Re-signed by the Tampa Bay Rays to a one-year contract. |
| 2019 | |
| 5/26/2019 | Contract purchased from Durham (AAA). |
| 3/22/2019 | Assigned by the Tampa Bay Rays to their minor league camp. |
| 1/18/2019 | Designated for assignment by the Tampa Bay Rays. |
| 1/04/2019 | Acquired from the Toronto Blue Jays |
| 2018 | |
| 12/30/2018 | Designated for assignment by the Toronto Blue Jays. |
| 11/26/2018 | Claimed off waivers from the Tampa Bay Rays. |
| 11/20/2018 | Designated for assignment by the Tampa Bay Rays. |
| 11/01/2018 | Claimed off waivers from the Minnesota Twins. |
| 8/04/2018 | Added to the Minnesota Twins 25-man roster. |
| 8/03/2018 | Claimed off waivers from the Toronto Blue Jays. |
| 7/30/2018 | Designated for assignment by the Toronto Blue Jays. |
| 7/27/2018 | Added to the Toronto Blue Jays 25-man roster. |
| 7/26/2018 | Claimed off waivers from the Los Angeles Angels. |
| 7/23/2018 | Designated for assignment by the Los Angeles Angels. |
| 7/06/2018 | Contract purchased from Salt Lake (AAA). |
| 6/19/2018 | Outrighted to Salt Lake (AAA). |
| 6/16/2018 | Optioned to Salt Lake (AAA). |
| 6/01/2018 | Added to the Los Angeles Angels 25-man roster. |
| 5/31/2018 | Claimed off waivers from the Cleveland Indians. |
| 5/26/2018 | Designated for assignment by the Cleveland Indians. |
| 5/08/2018 | Added to the Cleveland Indians 25-man roster. |
| 5/01/2018 | Designated for assignment by the Milwaukee Brewers. |
| 2017 | |
| 4/14/2017 | Acquired from the Baltimore Orioles. |
| 4/13/2017 | Designated for assignment by the Baltimore Orioles. |
| 4/02/2017 | Contract purchased from Norfolk (AAA). |
| 3/30/2017 | Outrighted to Norfolk (AAA). |
| 2016 | |
| 10/04/2016 | Not on the Baltimore Orioles Wild Card playoff game roster. |
| 8/28/2016 | Recalled from Norfolk (AAA). |
| 6/30/2016 | Optioned to Norfolk (AAA). |
| 6/21/2016 | Recalled from Norfolk (AAA). |
| 3/31/2016 | Optioned to Norfolk (AAA). |
| 2015 | |
| 9/15/2015 | Recalled from Norfolk (AAA). |
| 9/07/2015 | Optioned to Norfolk (AAA). |
| 9/01/2015 | Recalled from Norfolk (AAA). |
| 6/24/2015 | Optioned to Norfolk (AAA). |
| 6/21/2015 | Recalled from Norfolk (AAA). |
| 6/03/2015 | Optioned to Norfolk (AAA). |
| 5/23/2015 | Recalled from Norfolk (AAA). |
| 3/09/2015 | Optioned to Norfolk (AAA). |
| 2014 | |
| 11/18/2014 | Re-signed as a free agent by the Baltimore Orioles to a one-year contract. |
| 11/04/2014 | Opted for minor league free agency. |
| 2012 | |
| 11/20/2012 | Outrighted to Norfolk (AAA). |
| 11/02/2012 | Missed the last 5 regular season and all 6 playoff games (right shoulder tendinitis). |
| 10/07/2012 | Did not make the playoff roster. |
| 9/29/2012 | Right shoulder tendinitis, 60-day DL. |
| 9/29/2012 | Recalled from Bowie (AA). |
| 3/15/2012 | Optioned to Bowie (AA). |
| 3/10/2012 | Re-signed by the Baltimore Orioles to a one-year contract. |
| 2011 | |
| 11/18/2011 | Contract purchased from Bowie (AA). |
| 2008 | |
| 6/06/2008 | Drafted by the Baltimore Orioles in the 43rd round (1286th overall) in 2008. |
| 2019 | |
| 1/04/2019 | Toronto Blue Jays traded Oliver Drake to the Tampa Bay Rays for cash considerations. |
| 2018 | |
| 11/26/2018 | Claimed by the Toronto Blue Jays off waivers from the Tampa Bay Rays. |
| 11/01/2018 | Claimed by the Tampa Bay Rays off waivers from the Minnesota Twins. |
| 8/03/2018 | Claimed by the Minnesota Twins off waivers from the Toronto Blue Jays. |
| 7/26/2018 | Claimed by the Toronto Blue Jays off waivers from the Los Angeles Angels. |
| 5/31/2018 | Claimed by the Anaheim Angels off waivers from the Cleveland Indians. |
| 5/05/2018 | Milwaukee Brewers traded Oliver Drake to the Cleveland Indians for cash considerations. |
| 2017 | |
| 4/14/2017 | Baltimore Orioles traded Oliver Drake to the Milwaukee Brewers for a player to be named later or cash considerations. |
| 2008 | |
| 6/05/2008 | Drafted by the Baltimore Orioles in the 43rd round (1286th overall) in 2008. |
