Midfielder Rob Wolleaston joined Rushden & Diamonds from fellow Blue Square Premier rivals Cambridge United on a two-year deal for an undisclosed fee prior to the start of the 2008 / 09 season, at the age of 28.

Rob began his career at Chelsea and joined the U's from Oxford United in February 2006 after a spell at Bradford City. He made over 90 appearances for Cambridge, including scoring both the goals in the second leg of the Blue Square Premier play-off semi-final against Burton Albion which took his side to Wembley. During his time at Chelsea he also had a short loan spell at Northampton Town.

Rob missed the first few pre-season friendlies and the Maunsell Cup final at the start of the 2008 / 09 season as he recovered from injury, but made his debut at Nene Park in a friendly versus Derby County on 29th July 2008. Whilst still gaining match fitness, he went on to make his league debut by appearing as a substitute for the Diamonds in their 1-0 opening day victory over Eastbourne Borough on 9th August 2008. He scored his first goal for the club in the Diamonds 1-0 victory over Burton Albion on 20th September 2008.

With a late flurry of goals in the 2008-09 season, he finished the season as joint-top league goalscorer with 8 league goals, after appearing in 41 league games.