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.
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)