| Year | Date | Historical Events |
| 1939 | Dec 15 | Keel laid down at the Portsmouth Naval Shipyard, Kittery, ME. |
| 1940 | Sep 4 | Launched. |
| 1941 | Mar 1 | Commissioned. |
| | Mar 1 | Recommissioned. |
| | Jun 20 | Grayling was called upon to assist in the search for submarine 0-9, which had failed to surface after a practice dive off the Isle of Shoals. |
| | Aug 4 | Grayling sailed on shakedown cruise to Morehead City, NC., and St. Thomas, Virgin Islands. |
| | Aug 29 | Grayling returned to Portsmouth, NH. |
| | Nov 17 | Grayling departed Portsmouth,NH., armed at Newport, RI., and sailed for duty with the Pacific Fleet. |
| | Dec 3 | Grayling transited the Panama Canal. |
| | Dec 10 | Grayling arrived at San Diego, CA. |
| | Dec 17 | Grayling sailed for Pearl Harbor, HI. |
| | Dec 24 | Grayling arrived at Pearl Harbor, HI. |
| | Dec 31 | Grayling was chosen for the Pacific Fleet change of command ceremony. On that day Admiral C. W. Nimitz hoisted his flag aboard Grayling as Commander Pacific Fleet. |
| 1942 | Jan 5 | Grayling departed on her 1st war patrol. Cruising the Northern Gilbert Islands, Grayling failed to register a kill, but gained much in training and readiness. |
| | Mar 7 | Grayling returned to Pearl Harbor, HI. |
| | Mar 27 | Grayling departed on her 2nd war patrol. |
| | Apr 13 | Cruising off the coast of Japan itself, Grayling sank her first ship, sending the cargo freighter Ryujin Maru to the bottom. |
| | May 16 | Grayling returned to Pearl Harbor, HI. |
| | Jul 14 | Grayling began her 3rd war patrol. |
| | Aug 13 | Grayling damaged a Japanese submarine tender. |
| | Aug 26 | Grayling was forced to return to Pearl Harbor, HI. by fuel leaks.
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| | Oct 19 | Grayling departed on her 4th war patrol. |
| | Nov 10 | Although attacked by gunfire and six separate depth charge runs by Japanese destroyers, Grayling succeeded in sinking a 4,000 ton cargo ship southwest of Truk. |
| | Dec 4 | Grayling destroyed an enemy schooner. |
| | Dec 13 | Grayling arrived at Fremantle, Australia. |
| 1943 | Jan 7 | Grayling departed on her 5th war patrol,this time in Philippine waters. |
| | Jan 26 | Grayling sank the cargo ship Ushio Maru west of Luzon, Philippine Islands. |
| | Jan 27 | Grayling damaged another Japanese ship. |
| | Feb 24 | Grayling sank a schooner. |
| | Mar 1 | Grayling returned to Fremantle, Australia. |
| | Mar 18 | Grayling departed on her 6th war patrol and cruised in the Tarakan area and the Verde Island Passage. |
| | Apr 9 | Grayling sank the cargo ship Shanghai Maru and damaged four other ships. |
| | Apr 25 | Grayling returned to Fremantle, Australia. |
| | May 18 | Grayling departed on her 7th war patrol.Grayling patrolled the waters off northwest Borneo, where she damaged a freighter and two smaller ships. |
| | Jul 6 | Grayling returned to Fremantle, Australia. |
| | Jul 15 | Grayling began her 8th and last war patrol from Fremantle, Australia. |
| | Jul 31 | Grayling delivered supplies and equipment to guerrillas at Pucio Point Pandan Bay, Panay. |
| | Aug 23 | Grayling delivered supplies and equipment to guerrillas at Pucio Point Pandan Bay, Panay. |
| | Aug 27 | Grayling recorded her last kill, the passenger-cargo Meizan Maru in the Tablas Strait. |
| | Sep 9 | Grayling was lost between 9 and 12 September 1943 either in Lingayen Gulf or along the approaches to Manila. 76 men lost. |
| | Sep 30 | Decommissioned. |