Jeter took 25 dry swings and fielded 20 grounders hit right at him in Tampa on Monday. He also played long toss from 180 feet.
Jeter, who hasn't played yet this season, will continue to gain further clearance with the consultation from the Charlotte-based Dr. Robert Anderson, who performed the procedure last October.
The timetable for Jeter's return is still after the All-Star break and Cashman declined to put a more specific date on it. Cashman wasn't positive if Monday was the first time that Jeter had returned to the field since the Yankees announced he reinjured the ankle in the middle of April.
The Yankees have made their minor league facility largely inaccessible to the media, so this is the first time that anyone has known that Jeter was back on the field doing "baseball activities."
Jeter, who turns 39 on June 26, originally fractured the ankle during Game 1 of the Yankees ALCS loss to the Detroit Tigers. After the surgery, the Yankees and Jeter hoped he would return by Opening Day.
Instead Jeter suffered the small crack in the repaired ankle, causing him to miss at least the first half of the season.
In his place, the Yankees started with Eduardo Nunez as their shortstop, but Nunez has been on the DL now for a month with an oblique injury. Jayson Nix and Reid Brignac are currently the Yankees shortstops. Nunez also took grounders on the outfield grass Monday at the Yankees' minor league complex.
"We are running guys out there who are doing everything they can to help," Cashman said. "It is not the left side of the infield you typically would construct, but these guys are major league players. They are competitors and they are allowing us to hold the fort."
Outfielder Curtis Granderson, sidelined by a broken left hand, threw, but did not catch. He also ran in the outfield.
Information from The Associated Press was used in this report.