He was signed by Red Sox as non-drafted free agent on February 20, 2001. In his first year in 2001 he went 0–2 with 5.34 ERA in 10 games (eight starts) in the Dominican Summer League. He also participated in Fall Instructional League. Delgado missed the 2002 season due to elbow injury that required surgery on Ulnar Collateral Ligament, more commonly known as Tommy John surgery. He also missed the 2003 season recovering from the injury. He spent time with the Single-A Augusta GreenJackets and the Red Sox Gulf Coast League affiliate. Delgado went 1–5 with 5.22 ERA in 21 games (16 starts) with Augusta. He had a 2.77 ERA in 13 games on road, and 10.07 ERA in eight games at home. Placed on the disabled list from July 10 to August 22, and made one rehab start with the GCL Red Sox where he allowed two earned runs in 1.2 innings. Later that season, he participated in the Fall Instructional League and he also pitched for Aragua in the Venezuelan Winter League. In 2005 Delgado spent his entire season with the Single-A Greenville Drive, where he went 7–3 with two saves and 3.50 ERA in 33 games. \n', '

He was acquired from Red Sox with Hanley Ramírez, Aníbal Sánchez and Harvey García in exchange for Josh Beckett, Mike Lowell and Guillermo Mota on November 24, 2005.\n', '

On March 15, 2009, Delgado was claimed off waivers by the Seattle Mariners. \n', '

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