Sippio began playing professional football in 2002 with the Peoria Pirates of af2 and then the Greensboro Prowlers, before signing with the Arena Football League.
Sippio played in 15 games as a rookie with the Dallas Desperados, recording 75 receptions for 1,217 yards and 32 touchdowns, and recording 25.0 tackles, two interceptions and three passes broken up. He made his Arena Football League debut February 8 vs. the Carolina Cobras, catching four passes for 78 yards and two touchdowns. He was named co-Offensive Player of the GameMarch 6 against the Grand Rapids Rampage after catching 6 passes for 116 yards and three touchdowns. Sippio played in 16 games in his second season with Dallas, recording 61 receptions for 863 yards and 22 touchdowns and added 30.5 tackles, two interceptions and nine passes broken up. He scored touchdowns in five different ways during the season, receiving, rushing, interception return, fumble return and kickoff return.
Sippio played in nine games for the Tampa Bay Storm, recording 55 receptions for 666 yards and 18 touchdowns, before being released March 28 and claimed by the Chicago Rush on March 29.
Chicago Rush
After signing with Chicago, Sippio changed positions from WR/DB to OS. He finished the 2006 season with 93 receptions for 1,320 yards and 35 touchdowns. He recorded a season high 10 receptions for 136 yards and two touchdowns against the Orlando Predators on February 19. He also led the league with 53 touchdowns.
After the 2007 Arena Football League season, Sippio signed with the Kansas City Chiefs on August 12, 2007. His signing appeared on HBO's Hard Knocks, a program showcasing NFL training camps. On September 1, 2007 the Chiefs made their final cuts to 53, and Sippio made the final roster. However, he was released on September 2 to make room for Tyler Thigpen. The following day, Sippio was added to the Chiefs practice squad. He was signed to the active roster on September 11, 2007 to replace Eddie Kennison who suffered a hamstring injury. Sippio was released by the Chiefs on August 30, 2008.
On May 13, 2009, due to the injury of leading wide receiver Donovan Morgan, the Chicago Slaughter of the Continental Indoor Football League signed Sippio. The Arena Football League halted operations for the 2009 season, preventing Sippio from re-signing with the Rush or any other AFL team.
Sippio was signed by the Florida Tuskers of the United Football League on November 16, 2009. He played for then-head coach Jay Gruden.
Orlando Predators
Sippio signed with the Predators on April 13, 2010. Sippio scored 6 TDs, including a game-winner with just 8.7 seconds remaining, in Orlando's 73-69 victory over #1 seed Jacksonville in the first round of the 2010 Arena Football Playoffs.
Legal trouble
On May 25, 2012, Bobby Sippio was arrested and charged with attempted murder, armed robbery, aggravated battery, and kidnapping over an incident involving his girlfriend's brother. Sippio and a friend allegedly arrived at the man's apartment under the pretense of helping to move furniture, but instead they forced him into a vehicle at gunpoint, drove to an unpopulated area, then proceeded to beat and threaten the man before eventually returning him home. The man, Sergio Moore, suffered a broken nose, swollen left hand and wrist, and cuts to the head and cheek.
