It wouldn't be easy for Fife, as his pitching opponent was former Cy Young winner Roy Halladay, making his return to the Philadelphia Phillies' rotation after missing time with an injury. However, Fife held his own, throwing six innings, allowing just four hits and one run while walking three and striking out one. Fife was in line for the victory until the Dodger bullpen coughed up two runs in the top of the eighth, leaving him with a no-decision.
Fife pitched for the Drive early in the 2009 season, and he was very effective despite an 0-3 record. He recorded a 2.70 ERA in eight starts, and allowed 32 hits in 36.2 innings, but most impressively, Fife struck out 35 hitters while only allowing 4 walks before being promoted.
Fife was part of an extremely busy trade that saw his departure from the Red Sox organization in 2011. He was traded along with former Drive players Federowicz and Juan Rodriguez (2011) to the Dodgers in a three-way deal that sent major leaguer Erik Bedard from Seattle to Boston.