Erik MacArthur (Michael Stein) left the series after the first season to take a break and focus on school. Rather than hire another actor to be Michael, Steve Slavkin created a more charismatic jovial character named Ronny Pinsky played by Blake Sennett. Sennett was originally going to play Scotty Rex in "Telly's Tennis Match" but when MacArthur left the series, several rewrites were made.
Richard Williams (father of Venus and Serena Williams) served as the Tennis coach for Venus DeMilo (Telly) and Peter Ferrari (Scotty Rex).
Although Blake Soper (Sennett) is listed in the opening credits to "Telly's Tennis Match" he does not appear in the episode. This was the first episode filmed for season 2 and since Erik MacArthur left the series, Steve Slavkin had to do several rewrites. Sennett was originally slated to play Scotty Rex (Telly's Opponent) in the episode.
"Telly's Tennis Match" was satire of the real life Billy Jean King and Bobby Riggs "Battle of the Sexes" tennis match.
The unaccredited actor who plays the role of Tudgeman was actually a graduate student from Stanford working on the production staff.