5 - 1Y2K, You're Okay Sep. 22, 1999- 5 - 2Drew Goes to the Browns' Game Sep. 29, 1999
- 5 - 3Drew and the Gang Law Oct. 06, 1999
- 5 - 4Drew's Reunion Oct. 13, 1999
- 5 - 5Drew's Physical Oct. 20, 1999
- 5 - 6Drew Tries to Kill Mimi Oct. 27, 1999
- 5 - 7Red, White and Drew Nov. 03, 1999
- 5 - 8Drew Live Nov. 10, 1999
- 5 - 9Drew Cam Nov. 17, 1999
- 5 - 10Drew's Stomach Ache Nov. 24, 1999
- 5 - 11Steve and Mimi Get Married Dec. 01, 1999
- 5 - 12Drew and Kate's First Date Dec. 15, 1999
- 5 - 13Drew and the Racial Tension Play Jan. 05, 2000
- 5 - 14Kate Works for Drew Jan. 12, 2000
- 5 - 15Mimi Moves In Feb. 02, 2000
- 5 - 16Do Drew and Kate Have Sex? Feb. 09, 2000
- 5 - 17I Dishonestly Love You Feb. 16, 2000
- 5 - 18Drew Goes to Hell Feb. 23, 2000
- 5 - 19What's Wrong with This Episode III Mar. 01, 2000
- 5 - 20The Gang Stops Drinking Mar. 22, 2000
- 5 - 21Oswald's Son Mar. 29, 2000
- 5 - 22Mr. Wick Returns Apr. 12, 2000
- 5 - 23Kate vs. Speedy Apr. 26, 2000
- 5 - 24Beer Ball May. 03, 2000
- 5 - 25Drew and Kate Boink May. 10, 2000
- 5 - 26A Very Special Drew May. 17, 2000