Season Five of The Drew Carey Show premiered on September 22, 1999.
Episodes
| # |
#
|
Title
|
|
|
Airdate
|
|
|
|
| 102 |
1
|
Y2K, You're Okay
|
|
|
September 22, 1999
|
|
|
|
| 103 |
2
|
Drew Goes to the Browns' Game
|
|
|
September 29, 1999
|
|
|
|
| 104 |
3
|
Drew and the Gang Law
|
|
|
October 6, 1999
|
|
|
|
| 105 |
4
|
Drew's Reunion
|
|
|
October 13, 1999
|
|
|
|
| 106 |
5
|
Drew's Physical
|
|
|
October 20, 1999
|
|
|
|
| 107 |
6
|
Drew Tries to Kill Mimi
|
|
|
October 27, 1999
|
|
|
|
| 108 |
7
|
Red, White and Drew
|
|
|
November 3, 1999
|
|
|
|
| 109 |
8
|
Drew Live
|
|
|
November 10, 1999
|
|
|
|
| 110 |
9
|
Drew Cam
|
|
|
November 17, 1999
|
|
|
|
| 111 |
10
|
Drew's Stomachache
|
|
|
November 24, 1999
|
|
|
|
| 112 |
11
|
Steve and Mimi Get Married
|
|
|
December 1, 1999
|
|
|
|
| 113 |
12
|
Drew and Kate's First Date
|
|
|
December 15, 1999
|
|
|
|
| 114 |
13
|
Drew and the Racial Tension Play
|
|
|
January 5, 2000
|
|
|
|
| 115 |
14
|
Kate Works for Drew
|
|
|
January 12, 2000
|
|
|
|
| 116 |
15
|
Mimi Moves In
|
|
|
February 2, 2000
|
|
|
|
| 117 |
16
|
Do Drew and Kate Have Sex?
|
|
|
February 9, 2000
|
|
|
|
| 118 |
17
|
I Dishonestly Love You
|
|
|
February 16, 2000
|
|
|
|
| 119 |
18
|
Drew Goes to Hell
|
|
|
February 23, 2000
|
|
|
|
| 120 |
19
|
What's Wrong with This Episode III
|
|
|
March 1, 2000
|
|
|
|
| 121 |
20
|
The Gang Stops Drinking
|
|
|
March 22, 2000
|
|
|
|
| 122 |
21
|
Oswald's Son
|
|
|
March 29, 2000
|
|
|
|
| 123 |
22
|
Mr. Wick Returns
|
|
|
April 12, 2000
|
|
|
|
| 124 |
23
|
Kate vs. Speedy
|
|
|
April 26, 2000
|
|
|
|
| 125 |
24
|
Beer Ball
|
|
|
May 3, 2000
|
|
|
|
| 126 |
25
|
Drew and Kate Boink
|
|
|
May 10, 2000
|
|
|
|
| 127 |
26
|
A Very Special Drew
|
|
|
May 17, 2000
|
|
|
|
