Middleton has yet to play this season after undergoing wrist surgery over the summer, while Matthews has missed three straight games with a hamstring injury.
“(Middleton) has been making progress, probably steady and slow,” coach Mike Budenholzer said, via Eric Nehm of The Athletic. “Today was another good day. We’ll just continue to see how he feels. Hopefully, he can be doing a little bit more each day.”
Middleton, 31, is 6-foot-7 and a three-time All-Star, and widely viewed as the Bucks’ second-best player behind Giannis Antetokounmpo. He missed the Bucks’ second-round playoff series against the Celtics with the injury. They were initially hoping he could return in November, but that timeline may be delayed a little.
Last season, he averaged 20.1 points and 5.4 rebounds in 66 games, shooting 44 percent from the field. He has averaged at least 20 points in each of the past three seasons.
Originally selected by the Pistons in the second round of the 2012 draft, Middleton has spent all but his first season with the Bucks.
Matthews, 36, is 6-4 and is averaging 3.4 points in 13 games this season, his second in a row in Milwaukee and third overall. He has also spent time with the Lakers, Knicks, Mavericks, Pacers, Trail Blazers and Jazz.