Nathan moved up from the reserves in the 2002/03 season and made his debut, as a substitute, on 15/03/2003 at home to Erith Town. This was Nick Denly’s last game in charge, although his departure had nothing to do with the selection of Nathan.

The following campaign, under Simon Bryant, Nathan was on the fringe of the squad making his first start for Herne Bay, in the Kent Senior Trophy against VCD Athletic at Winch’s Field on 04/10/2003 where he scored the first goal for the club in the 2-3 defeat. A week later he scored his first league goal, as a substitute, in the 3-0 home win over Lordswood. Nathan’s first league start was away at Thamesmead Town on 16/03/2004.

With Jason Lillis taking the helm for 2004/05 Eastwood became a regular in the team and on 29/01/2005 Bay beat Erith Town at home 6-1 which included a Danny Kedwell hat-trick and a bizarre incident. With the Docker’s Aran Hayrettin lying hurt in the Erith penalty-area, one of his teammates hammered the ball out of play so he could receive attention. When play resumed from Bay’s throw, Nathan Eastwood took possession and, in keeping with the normal – if unwritten – practice, sportingly aimed the ball in the direction of goalkeeper Chris Arnold. Unfortunately, Eastwood appeared to miss-hit his back-pass. Arnold was caught on the hop and, despite his desperate attempt at retrieval, the ball ended up in the net. Under the rules, the goal was awarded. Bay captain Ronan O’Connor asked the referee if the goal could be disallowed but he said that he couldn’t do that. Herne Bay then made no attempt to intervene as Alan Hanlon, wearing a faintly bemused air, strolled through the stationary ranks from the centre-circle and prodded the ball into an empty net. Lillis had instructed his players not to do anything to prevent Erith equalising from the restart. “I just felt it was the right thing to do,” he said.

In 2005/06 Nathan made his 50th league and cup appearance, away at Thamesmead Town on 17/09/2005 and then scored twice in the Kent League Premier Division Cup on 21/01/2006 at home to Sporting Bengal. He was again on the scoresheet in his 50th league appearance, away at Hythe Town on 25/02/2006.

In Jason Lillis’ third season at the helm Nathan played a more defensive role and notched up a further 29 appearances. The most eventful match came on 11th November 2006 when Beckenham Town visited Winch’s Field. One of the assistant referees failed to show and Bay assistant manager Terry Sedge took the flag. Beckenham arrived at the ground late and Herne Bay were awarded a penalty after 5 minutes when referee Simon Finnigan adjudged Sam Denly to have been brought down in the box and Richard Dimmock struck home from 12 yards. On the half hour mark Beckenham equalised and just before the break Nathan Eastwood was hacked down with Finnigan showing a red card and a major fracas ensued. Denly was struck and Becks’ physio ran around throwing punches at anyone in blue. The whole Beckenham bench, plus a number of spectators were on the pitch and the police were called to calm down the situation. The game restarted with the visitors down to nine men and no physio. With Beckenham parking the bus in the second half new contract player Aaron Firth scored Bay’s winner in the 75th minute. He made his 100th league and cup appearance, away at Sporting Bengal on 24/03/2007.

Jason Lillis resigned before the end of the season and reserve’s manager Barry Morgan took over. Nathan then took a season out from competitive football in 2008/09, although he played a few Sunday league games. When he returned in 2009/10 it was for Faversham Town – we can allow everyone one mistake!

With Barry Morgan relieved of his duties in October 2009 following a defeat to…Faversham, Simon Halsey took over as manager and by March 2010 Nathan was back at Winch’s Field and made his return debut on 02/03/2010 away at Deal Town and on 10/03/2010 made his first start in the Kent League Premier Division Cup at home to…Faversham.

Bay finished as runners-up in the league and won the Kent League Premier Division Cup, beating Sevenoaks Town 3-2 after extra time with Eastwood making an appearance as a substitute.

In 2010/11 Herne Bay again finished as runners-up in the league, this time to Hythe Town, but with Nathan in the starting line-up Bay beat the Forters in the final of the Kent League Premier Division Cup. Eastwood’s 100th league appearance came away at Hythe Town on 04/09/2010 and two weeks later he made his 150th league and cup appearance, at home to VCD Athletic on 18/09/2010. Nathan scored his last goal for Herne Bay on 17/04/2010 at home to Fisher.

In 2011/12, after 38 seasons in the Kent League, Herne Bay won the title for the fifth time and on this occasion were in a position to take the promotion into the Isthmian League. Bay also reached the semi-final of the FA Vase, one step away from Wembley.

He made his 200th league and cup appearance, at home to Beckenham Town on 28/04/2012. On 02/02/2013 Nathan made his 150th league appearance, away at Tooting & Mitcham United. 11 matches later, Manager Simon Halsey, was sacked and Eastwood made two appearances under caretaker Anthony Deer.

For 2013/14 Herne Bay appointed Sam Denly as their new manager. Sam is the son of Nick, under whom Nathan made his debut in 2004. Eastwood and Sam Denly were in the same Herne Bay team until 2008 when Denly departed from the club. There were some significant milestones as Nathan made his 250th league and cup appearance, at home to Redhill on 16/11/2013 and his 50th league and cup appearance since joining the Isthmian League, at home to Redhill on 16/11/2013. And on 15/03/2014 he made his 50th Isthmian league appearance, away at Redhill.

In 2014/15 Nathan made his 200th league appearance, away at Burgess Hill Town on 20/09/2014 and his 300th league and cup appearance, at home to Whitstable Town on 06/04/2015. Then on 25/04/2015 he made his 100th league and cup appearance since joining the Isthmian League, away at Whyteleafe.

During 2015/16 Nathan made his 100th Isthmian League appearance, at home to Walton Casuals on 21/11/2015. There was then a 250th total league appearance, away at Walton Casuals on 02/04/2016. This was also going to be Eastwood’s last match for Herne Bay as he announced his retirement after 339 appearances.

Nathan signed Ryman League forms for Herne Bay for the 2016/17 season...but only as a back-up. With a defensive injury crisis he was soon back in action and reached the magical 350 mark.