Birthdate: March 1, 1963
Married to Clare Chalupsky and has two children, Luke, 18 and Hannah, 15
Height: 6'4"
Weight: 260 lbs. off training weight and 220 lbs. in training weight

Few paddlers hold a record comparable to that of Oscar Chalupsky. Beginning his canoeing career during his school years, his list of accomplishments includes twelve-time World Surf Ski Champion, multiple winner of the Umkomaas River Marathon, and Olympic Canoe Team captain and participant, representing South Africa in the 1992 Barcelona Olympics.

Oscar's achievements are endless and his decision to embark on the Chalupsky Paddle School is based on the aspiration of opening up the sport of kayaking to everyone. Oscar's skills coupled with some of Natal's finest canoeing rivers and venues make the Chalupsky Paddling School a unique outdoor attraction. Oscar's experience makes him an ideal instructor to all aspiring paddlers, both those who are trying out the sport for the first time, as well as the seasoned race participant.

1979

• Youngest Springbok/South African Lifesaver Victorious in test against U.S.A
• Won all South African Junior sprints canoeing from U16, U18

1980

• First person in the world and in the history of Surf Lifesaving to win Junior and Senior Iron Man
• Represented: Natal Schools Rugby
• Natal Schools Water Polo
• South African Schools Water Polo
• Natal Senior Canoeing Team
• Third South African Wild Water Champs

1981

• First person in the world and in the history of Lifesaving to win Junior and Senior Victor Ludorum
• Youngest person to win 244 km Port Elizabeth to East London Paddle Ski/Ocean Kayak Race
• Junior Springbok/South African Water Polo Team, successful tour to Israel
• Youngest Springbok/South African Canoeist
• Second in Sella Descent, Biggest Canoe Race in the world held in Spain
• South African Junior Sportsman of the year

1982

• Victorious in Springbok/South African Lifesaving Team test against U.S.A.
• Natal Water Polo Team
• South African Iron Man Champion
• South African Paddle Ski / Ocean Kayak Champion

1983

• Winner of World Paddle Ski/Ocean Kayak Championships (Molokai to Oahu, Hawaii), beat four-time winner Grant Henny from Australia, who won Bronze Olympic Medal
• Winner of 244 km Port Elizabeth to East London Paddle Ski/Ocean Kayak Race
• Springbok/South African Lifesaving Team
• Springbok/South African Paddle Ski/Ocean Kayak Team
• South African Body Boarding Champion
• South African K1 Canoeing Champion
• Natal Sportsman of the Year

1984

• Second-time winner of World Paddle Ski/Ocean Kayak Championships in Hawaii
• South African Iron Man Champion
• Springbok/South African Paddle Ski/Ocean Kayak Champion
• South African Ski Champion

1985

• Third-time winner of World Champion Paddle Ski/Ocean Kayak in Hawaii
• World Canoeing Champion, Spain, Sella Descent, 2000 participants and 500 000 spectators
• Winner of 244 km Port Elizabeth to East London Paddle Ski/Ocean Kayak Race
• Springbok/South African Canoeing Team
• Springbok/South African Paddle Ski/Ocean Kayak Team
• Second place in Berg River Canoe Marathon
• South African K2 Canoeing Champion
• Third place in Dusi Canoe Marathon
• South African Paddle Ski / Ocean Kayak Champion

1986

• Fourth-time winner of World Paddle Ski/Ocean Kayak Championships in Hawaii
• Springbok/South African Canoeing, Lifesaving and Paddle Ski/Ocean Kayaking
• South African K2 Canoeing Champion
• Winner of South African Premier Down River Canoeing Race, Umkomaas Marathon
• Second place by one second in the Sella Descent, held in Spain
• South African Iron Man Champion
• South African Paddle Ski/Ocean Kayak Champion

1987

• Fifth-time winner of World Paddle Ski/Ocean Kayak Championships in Hawaii
• Springbok/South African Lifesaving, Canoeing and Paddle Ski/Ocean Kayaking Teams
• Winner of Australian Paddle Ski/Ocean Kayak Race in Newcastle
• South African Paddle Ski/Ocean Kayak Champion Winner Umkomaas Canoe Marathon

1988

• Sixth-time winner of World Paddle Ski/Ocean Kayak Championships in Hawaii
• West German National Canoeing Team
• Springbok/South African Lifesaving, Canoeing and Paddle Ski/Ocean Kayak Teams
• Third in SOUTH AFRICAN K2 Canoeing Championship
• Winner of 244 km Port Elizabeth to East London Paddle Ski/Ocean Kayak Race
• SOUTH AFRICAN Paddle Ski/Ocean Kayak Champion

1989

• Seventh-time winner of World Paddle Ski/Ocean Kayak Championships; neat double Gold Olympic Medalist Greg Barton (USA), in World Paddle Ski/Ocean Kayak Champs
• Springbok/South African Lifesaving Captain; successful tour to Taiwan against Australia, Hong Kong, Taiwan and Japan
• Springbok/South African Paddle Ski/Ocean Kayak Colours
• First place in Umkomaas Marathon
• South African Iron Man Champion

1990

• One of 10 Finalists in 'Sportsman of the Decade'

1991

• Reduced golf handicap from 24 to 4 (sporting isolation year).

1992

• Springbok/South African Lifesaving Team; tour to Australia
• Olympic Canoe Team, Barcelona, Spain
• Olympic Captain

1994

• Eight time Winner of World Paddle Ski/Ocean Kayak Championships in Hawaii
• Winner of the Port Elizabeth, East London Paddle Ski/Ocean Kayak Race

1996

• Winner of the Port Elizabeth, East London Paddle Ski/Ocean Kayak Race

1997

• Completed Dusi Canoe Marathon, Pietermaritzburg to Durban, with Naas Botha (former South African rugby great)

1998

• Winner of the Heineken International Paddle Ski/Ocean Kayak Race, Tahiti, French Polynesia
• Winner of the 244 km Port Elizabeth , East London Paddle Ski/Ocean Kayak Race
• Completed Dusi Canoe Marathon, Pietermaritzburg to Durban, with Clive Barker (former South African soccer coach)

1999

• Second in World Paddle Ski/Ocean Kayak Championships in Hawaii
• Winner of the Heineken International Paddle Ski/Ocean Kayak Race, Tahiti, French Polynesia
• Second in 60km World Sea Kayak Championships, Canada; second to brother Herman by 10 seconds
• Winner of International Ocean Kayak Race, on the Chao Praya River, Bangkok, Thailand
• Winner of International Ocean Kayak Race in Miami, Florida
• Completed Dusi Canoe Marathon, Pietermaritzburg to Durban, with Doctor Khumalo (South African soccer player)

2000

• Ninth consecutive win at World Paddle Ski/Ocean Kayak Race in Hawaii
• Winner of 65 km Cape Point Ocean Kayak Race Cape Town
• Third Place in the Heineken International Paddle Ski/Ocean Kayak Race, Tahiti, French Polynesia
• Completed Dusi Canoe Marathon, Pietermaritzburg to Durban, with Peggy Sue Khumalo (former Miss South Africa)

2003

• Record tenth win at the Molokai World Surf Ski Championship

2004

• Finished second at the Molokai World Surf Ski Championship

2005

• Record eleventh win at the Molokai World Surf Ski Championship

2006

• Finished second at the Molokai World Surf Ski Championship