| Category |
Run |
Date |
Winner(s) |
Location |
| Best Run |
1892 |
30 Sep 2009 |
Wet Pet & Father Anus |
Dairy Farm Road |
| Longest Run |
1893 |
7 Oct 2009 |
Shaggy Dick Too & Royal Tit |
Blackmore Drive |
| Shortest Run |
1910 |
27 Jan 2010 |
Aussies: Cock Radio, Maggot, Sneaky Comer |
Mayfair Park |
| Wettest Run |
1900 |
18 Nov 2009 |
Committee: Tiger Lily & Legolas |
Sentosa, Tanjong Beach |
| Most Scenic Run |
1887 |
26 Aug 2009 |
Give Way & Not Good Enough |
Telok Blangah |
| Most Creative Run |
1897 |
28 Oct 2009 |
Shoe Shopper & Wet Patch |
Mount Sinai Rise |
| Most Confusing Run |
1901 |
25 Nov 2009 |
Kannot Kan & Hooray |
Swiss Cottage Estate |
| Best On On |
1876 |
10 Jun 2009 |
The Stiff Family |
10 Maida Vale |
| Best Drink Stop |
1879 |
1 Jul 2009 |
Virginia Slim & Big Head |
Upper Seletar Reservoir |
| Harriets' Hero |
|
|
Cock Radio |
|
| Most Laid Harriet |
|
|
Shoe Shopper |
|
| Unsung Hero |
|
|
Sneaky Comer |
|
