Hilliard signed with the Tampa Bay Buccaneers after the 2004 season. During his first two seasons with Tampa Bay, he was used mainly as a third or fourth receiver, but in 2007 he started ten games making sixty-two receptions for 722 yards. During his time with the Bucs, he became a third down specialist, 111 of 178 career catches resulting in a 1st down. Head Coach Jon Gruden referred to him as "Third and Ike". On October 19, 2008, Hilliard refused to be carted off the field during a Sunday Night Football 20-10 win over the Seattle Seahawks after a helmet-to-helmet hit by Seattle linebacker Leroy Hill, who hit Hilliard in a head-on collision as Seahawks linebacker Lofa Tatupu hit him from behind, forcing his body to go limp after making a catch in the second quarter.