In September 1905, Eastham moved to Glossop where he played in either full-back position, making 26 appearances as the club finished near the foot of the Second Division table.
[2] In 1907–08, Eastham settled into the right-back role, although he missed two long periods through injury (when the versatile John Robertson took over) making 22 appearances in all as the "Saints" finished eleventh in the league.
[3] In the FA Cup, Eastham played in all six matches as the Saints made it through to the semi-final, after a replay in round 4, when they defeated the previous season's runners-up Everton 3–2 (including two goals from Frank Costello).
[4] In the semi-final itself, played at Stamford Bridge on 28 March 1908, the Saints were defeated by Wolverhampton Wanderers, with goals from former Southampton players Wally Radford and George Hedley.
The Monday night match was poorly attended with Portsmouth playing a team consisting mainly of reserve players, who nonetheless kept the score down to 2–1, with Southampton's goals coming from Hamilton and McAlpine.