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numerista
19 Jul 2006, 12:50 AM
Winningest MLS Coaches All-Time
(through 7/18/06, shootouts count as ties, minimum 25 games)

Arena 49-25-22 0.625
Nowak 40-21-20 0.617
Kinnear 35-17-27 0.614
Yallop 44-27-21 0.592
Zambrano 75-51-17 0.584
Schmid 82-59-41 0.563
Bradley 115-85-58 0.558
Nicol 54-45-34 0.534
Andrulis 49-43-33 0.524
Hudson 46-42-20 0.519
...
other active coaches
Clarke 35-32-19 0.517
Sarachan 43-40-26 0.514
Gansler 86-85-51 0.502
Clavijo 42-50-22 0.465
Ellinger 9-31-9 0.276

EDIT to add: I haven't checked the frequency of draws, but it does seem different for different coaches.

numerista
19 Jul 2006, 09:59 AM
The Eight Winningest Coaches by Year

1996 (1 of 8 in MLS)
Bruce Arena, DC - Champion

1997 (2 of 8 in MLS)
Bruce Arena, DC - Champion & Supporters' Shield
Octavio Zambrano, LA

1998 (3 of 8 in MLS)
Bob Bradley, Chi - Champion
Bruce Arena, DC - Runner-Up
Octavio Zambrano, LA - Supporters' Shield

1999 (2 of 8 in MLS)
Sigi Schmid, LA - Runner-Up (took over early-season)
Bob Bradley, Chi
(Nicol was briefly an interim in NE; Zambrano fired early in LA.)

2000 (3 of 8 in MLS)
Bob Bradley, Chi - Runner-Up
Sigi Schmid, LA
Octavio Zambrano, NY

2001 (4 of 8 in MLS)
Frank Yallop, SJ - Champion
Sigi Schmid, LA - Runner-Up
Bob Bradley, Chi
Octavio Zambrano, NY

2002 (5 of 8 in MLS)
Sigi Schmid, LA - Champion & Supporters' Shield
Steve Nicol, NE - Runner-Up (took over mid-season)
Bob Bradley, Chi
Frank Yallop, SJ
Octavio Zambrano, NY

2003 (4 of 8 in MLS)
Frank Yallop - Champion
Bob Bradley, NY
Steve Nicol, NE
Sigi Schmid, LA

2004 (5 of 8 in MLS)
Peter Nowak, DC - Champion
Bob Bradley, NY
Dominic Kinnear, SJ
Steve Nicol, NE
Sigi Schmid, LA (fired mid-season)

2005 (4 of 8 in MLS)
Steve Nicol, NE - Runner-Up
Dominic Kinnear, SJ - Supporters' Shield
Bob Bradley, NY (fired late-season)
Peter Nowak, DC

2006 (7 of 8 in MLS)
Bruce Arena, NY (took over mid-season)
Bob Bradley, Chv
Dominic Kinnear, Hou
Peter Nowak, DC
Steve Nicol, NE
Sigi Schmid, Clb
Frank Yallop, LA (took over mid-season)