The sport of Brazilian jiu jitsu has provided us fans, years of entertainment with exciting comebacks and upsets that have helped develop this incredibly intricate martial art. Although the Gracie’s tried hard to broadcast the jiu jitsu style since early on, organizing the very first Rio de Janeiro State federation in 1967 in a combined effort with some of the region’s top coaches, for years the sport lacked a solid organization skills and numbers in athletes. In the mid 1980’s the sporting side of jiu jitsu started blossoming thanks to the efforts of men such Robson Gracie, and later Carlos Gracie Junior. With the numbers of athletes, more tournaments developed. This represented more platforms to perform, which ultimately meant more talent on display, leading to a solid fan base. On this article, we will go through 10 of the biggest upsets in Brazilian jiu jitsu. Matches that left fans scratching their heads, while reshaping our perception of the top contenders and our understanding of the sport. Top 10 Biggest Upsets in Brazilian Jiu Jitsu 10. JOSÉ (ZÉ) MARINHO vs OSWALDO FADDA The match happened on the 1st round of the very first Rio State Championship (1950). The tournament was organized to help promote jiu jitsu and was under a “submission only” format, set to decide who were the top grapplers in Rio. Although Marinho was a solid student of Helio Gracie, Oswaldo Fadda (29 years old) was one of the most prestigious coaches in the region, and regarded as a tough test to Pedro Hemetério (Gracie Academy’s top student). Unfortunately for Fadda, his progress in the competition was stopped as he dislocated his shoulder after a violent throw from Zé Marinho. The tournament was eventually won by 17 year old revelation, Carlson Gracie. 9. SERGIO MORAES vs KRON GRACIE In 2008 Kron Gracie was regarded as one of the most accomplished brown belts in the history of jiu jitsu, one who had a 51 straight submission win streak. Being graded to black belt only a couple of weeks before the World Championship, the world awaited to see Rickson Gracie‘s son take his crown as king of the middleweight division. In his first round, Kron drew against Sergio Moraes. Serginho had received his black belt the year before, but had been sidelined due to a knee injury and was virtually unknown to the mainstream BJJ fans, who saw Serginho as a stepping stone towards gold. Sergio Moraes shocked the world by totally dominating the young Gracie, submitting him with an arm in ezekiel and going on to win the tournament. 8. BOB BASS vs MÁRCIO FEITOSA The only match of brown belt vs brown belt on this list happened in 1995 at the Pan American Championship. Márcio Feitosa was one of the most dominant brown belts the lightweight division had ever witnessed. Undefeated, and regarded as Carlos Gracie Junior‘s most talented pupil, Feitosa matched against Rigan Machado‘s student Bob Bass, who was virtually unknown to the majority of jiu jitsu fans and followers. Bass put on an incredible performance, showing that he belonged among the best, passing Márcio’s guard and securing the victory by 3×0. Feitosa would avenge the loss the following year, while Bob would become one of the first men outside Brazil to achieve the rank of black belt in jiu jitsu. 7. ROBERTO (ROLETA) MAGALHAES vs JOSÉ MARIO SPERRY Roberto “Roleta” Magalhaes and Zé Mario Sperry clashed twice at the 1998 World Jiu Jitsu Championship, one of the most exciting jiu jitsu events ever. In the super heavyweight division, Sperry and Roleta clashed in the ¼ finals. A much anticipated match between the best guard passer in the sport against the modern day guard player. Sperry’s excellence is not truly grasped today. Mario had never tasted defeat in a jiu jitsu match. Ever. He hadn’t even had a point scored against him until reaching black belt. This didn’t stop Roleta, who managed to impose his game plan and submerge Sperry into his quicksand type guard, nudging a win on points, ending a long winning streak. Zé Mario avenged his loss on that same tournament, in the absolute division. Roleta would also be the only man to have defeated Amauri Bitetti with the gi. A win by 2×0 at the 1999 World Championships. 6. HAROLDO (CABELINHO) BUNN vs JEAN JACQUES MACHADO This match happened in the ¼ final of the CBJJ (now IBJJF) World Jiu Jitsu Championship of 1999, middleweight division. When looking at the brackets at the time, most guessed Jean Jacques would meet against Alexandre Paiva in the semi final of the event, but 22 year old Haroldo “Cabelinho” thought otherwise. After winning his first two matches by submission, Machado met a very game opponent in Haroldo, who sneaked a win by kneebar (video below). 5. LEANDRO LO vs MICHAEL LANGHI Leandro Lo arrived at the 2011 Abu Dhabi World Pro, as your average “meat for the grinder” black belt, and left as one of the hottest prospects in the sport. His win over Langhi, who hadn’t tasted defeat in over 3 years, set him up to be what he is today. One of the best athletes of all time. The two met at the semi final of the event, where Lo stole the win by taking Michael’s back, securing the 4 points (4×0 in the end). Leandro would face another dominant lightweight in the final, Celso Vinicius, beating the Ryan Gracie head coach on advantages. 4. RODOLFO VIEIRA vs BRAULIO ESTIMA The match occurred at the 2009 Abu Dhabi World Pro Championship in the 94 kilogram mixed (brown and black belt) division, and it placed a young brown belt on the jiu jitsu map. In a stellar performance throughout the tournament, Rodolfo defeated some of the top black belts in the world, putting on a clinic of heavy top pressure. The most accomplished black belt defeated by the young GFTeam star was Braulio Estima, a 3x black belt world champion who was regarded as the favorite to win the tournament. Rodolfo Vieira went through on advantages. 3. DEAN LISTER vs SAULO RIBEIRO Although Lister had competed at the ADCC prior to 2003, he was not regarded as a big player, having never past the quarterfinals. In 2003 Lister had been concisely defeated in his weight class by Xande Ribeiro (8×0), and wasn’t expected to be called in for the open weight. Good thing he was, as this event truly boosted Lister’s career and recognition as one of the top grapplers in the world. Dean Lister met 4x world jiu jitsu champion Ribeiro on the ¼ finals of the tournament, submitting the legendary jiu jitsu master with an unexpected kneebar. Lister would cement his status with a victory over Pé de Pano at the semi final and Alexandre Cacareco in the final. 2. EDDIE BRAVO vs ROYLER GRACIE Another relatively unknown American who shocked the jiu jitsu world at the 2003 ADCC finals. Bravo was a brown belt at the time, who secured his spot in the tournament by winning the US trials. He met 4x World Champion, 3x ADCC champion and all around legend of the sport, Royler Gracie in the ¼ finals of the event. Bravo frustrated Royler Gracie’s famous knees-slide guard pass attempts with great guard recovery skills and manage to sink in a triangle choke, which ended the match. Eddie went on to become a successful instructor at his own 10th Planet Jiu Jitsu academy. 1. MACKENZIE DERN vs GABRIELLE (GABI) GARCIA Arguably the biggest upset of all time. Mackenzie Dern weight in at 55kg against Gabi’s 100kg (estimate). To add to this amazing achievement, Garcia hadn’t lost a match since 2009 as a brown belt. Furthermore, the two had met on previous occasions, all losses by submission to Dern. That day was different. Showing tremendous mental fortitude Mackenzie put on her game face and dragged Garcia into her open guard, where pulled of the win with a negative point (0x0 on the board), leaving the stands in awe.