Pools were struggling for goals when Freestone arrived and this trend continued as his first two games were defeats in which he (and the team) failed to find the net. His first goal for the club was to come in a vital 2-0 home win against Chester City. He added two more in a crucial 3-0 victory in a key relegation battle with Scarborough. Freestone`s goals and general play were an important feature of Pools`s run-in as the team hauled themselves out of trouble. By the time the last game of the season was played, survival was assured and Pools could relax while Carlisle goalkeeper Jimmy Glass`s last minute goal relegated Scarborough.
The following season saw Freestone drift in and out of the team and he regularly found himself on the bench while Jones and Kevin Henderson played up front and Tommy Miller supplied the goals from midfield. With chances limited he had a brief loan spell at Cheltenham Town but returned to the club for the last few games of the season. His last appearance for the club was a surprise recall for the second leg of the 1999/00 playoff semi-final at Darlington. Pools lost that game, and Freestone never played for the club again. He joined Shrewsbury Town in the close season but, after failing to hold down a regular place at Gay Meadow, slipped into non-league football.