During Week 6 in 2001, Robert Segedin competed at Cooperstown Dreams Park with the Jersey Bandits (NJ). Robert's high school baseball career took place at Northern Valley Regional High (Demarest, NJ), where he was a four-year letter winner. During his four years, Robert helped his team to a combined 101-23 record, winning the state sectional title as a junior, finishing sectional and county-runner up as a sophomore and senior, and claiming the county championship as a freshman. Robert earned all-league honors all four years (second-team as a freshman and first-team his final three seasons), second-team all-county as a sophomore and named New Jersey Hitter of the Year and first-team all-state and all-county as a junior and senior. He set the New Jersey state record with 181 career hits. Robert's high school stats include a .520 BA with four home runs and 31 RBI and went 10-0 with a 1.35 ERA and 64 strikeouts on the mound, during his senior year. He went .560 with eight doubles, eight triples, eight home runs and 39 RBI as a junior, a .483 BA with 17 doubles, three homers and 31 RBI as a sophomore and a .398 BA as a freshman. Robert also played for the Bayside Yankees (NY) where he helped the club win the Premier Baseball National Championship in 2006 and 2007, and was named team MVP in 2006. In addition to baseball, Robert was a member of National Honor Society, served as class vice president and graduated Magna Cum Laude.

After his high school graduation, Robert continued his baseball career, playing for and attending school at Tulane University (New Orleans, LA). During his freshman season (2007), Robert played in all 62 games, including 61 starts at third base. He was named second-team All-Conference USA and claimed a spot on the C-USA All-Freshman Team. Robert tied for team highs with a batting average of .322 and 18 doubles, while leading the club in hits (75) and RBI (59) and ranked second for on-base percentage (.414), third in total bases (113) and slugging percentage (.485) and tied for fifth in home runs (six). Robert also made an impact from the mound, appearing in 14 games out of the bullpen where he has a win, five saves and 21 strikeouts in 19.1 innings. Robert was ranked tied for sixth in C-USA in doubles, RBI and saves. He led Tulane with 21 multiple-hit games and 19 multiple-RBI contests. He was named C-USA Co-Hitter of the Week and earned a spot on the College Baseball Foundation National All-Star Lineup on April 21 after hitting .600 (9-for-15) with two home runs and seven RBI during his time at the plate while also posting a pair of saves, a .071 opponent batting average (1-for-14) and a flawless 0.00 ERA in two appearances and 4.0 innings of work on the mound.

Unfortunately, a back injury during his sophomore year (2008) sidelined Robert for the majority of the season – he received a medical red shirt. Appearing in only five games, Robert posted a .286 BA (four-for-14) with three doubles and four runs batted in and tallied five walks in four games for a .476 on-base percentage.

Considered a red shirt sophomore in 2010, Robert was back on the field healthy. He started 55 games at third base, leading the team in batting average (.434), slugging percentage (.788), on-base percentage (.516), runs scored (55), hits (92), RBI (54), doubles (29), home runs (14), total bases (167) and hit-by-pitch (5). Hew was tied for the team in walks (33), tied for second in stolen bases (4) and triples (2), and tied for third in starts (55). Robert earned First Team All-Conference USA, named Conference USA Hitter of the Week on March 22, and led Conference USA in doubles (29).

In June of 2010, the New York Yankees drafted Robert in the third round of the Major League Baseball Amateur draft. Robert played in the Rookie League with the GCL Yankees (Tampa, FL) after the 2010 draft and then the short season A Staten Island Yankees (Staten Island, NY). He started the 2011 season with the Class A Charleston RiverDogs (Charleston, SC) and finished with Class A+ Tampa Yankees (Tampa, FL) where he began the 2012 season before moving to AA Trenton Thunder (Trenton, NJ).