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Over the years, Outward Bound Singapore has garnered local and international awards in recognition of the continuous efforts we have put in to maintain our high standards in the field of experiential learning, creativity and innovation.
| 2003 | Leader Mentor Award to Winston Lim at Global Leaders Mentoring Congress. |
| 2002 | - Winner of NOVA Award for artificial Tunnel/Cave/Maze (TCM).
- Winner of Innovative Programming Award from Outward Bound International for artificial Tunnel/Cave/Maze (TCM).
- Distinguished Service Award to Winston Lim from Outward Bound International.
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| 2001 | - Winner of Innovative Programming Award from Outward Bound International for Overseas Youth Programme.
- Special Commendation Award in Innovative Programming from Outward Bound International for SPARKc .
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| 2000 | - Excellence for Singapore Award from Singapore Totaliser Board.
- Distinguished Service Award from Outward Bound Indonesia.
- Leadership Award to Winston Lim from Outward Bound International.
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| 1997 | - OBS Spirit Award (International) from Chairman of Outward Bound International.
- Spirit of the Outward Bound Award from Chairman of Outward Bound Australia.
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| 1995/6 | - Pin of Honour Award to Winston Lim from Outward Bound International
- 12 Friends of Schools Award
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