Middleton underwent an arthroscopic clean-up procedure on each ankle during the offseason, Shams Charania of The Athletic reports.

Middleton had left ankle surgery shortly after Milwaukee's playoff exit, then had his right ankle operated on in mid-June. The surgeries were deemed a success and were necessary to help Middleton get rid of his lingering soreness in both. The good news for the Bucks is that Middleton is expected to be ready for the start of the 2024-25 campaign. During the 2023-24 regular season, Middleton was limited to 55 games and produced averages of 15.1 points, 4.7 rebounds, 5.3 assists and 1.7 three-pointers.