1) Macclesfield Town 2 Torquay United 1, 9th August 1997
The opening day of the 1997-98 campaign was a day of many firsts for both Torquay United and Macclesfield Town. The Silkmen, who had won promotion to the Football League after winning the Conference title in the 1996-97 season, were playing their first fixture as a league club.
Torquay - then managed by Kevin Hodges - were fielding a whole host of new signings, including a young midfielder signed for Torrington Town on the recommendation of Hodges' former Plymouth Argyle boss Johnny Hore by the name of Kevin Hill.
'Hilly' made the first of what would be a club record total of 474 games for United when he came on as a second half substitute for fellow debutant Paul Gibbs in a game that the Gulls lost 2-1, as Efe Sodje and former Plymouth striker Richard Landon scored for the Silkmen and Andy Gurney replied for United.
2) Barnet 2 Torquay United 3, 5th May 2001
In their final fixture of the 2000-01 season, Torquay travelled to Underhill to face in a 'do or die' relegation decider that would see the loser drop into the Conference. After winning the club's Player of the Year award on what would be the first of two occasions in the previous campaign, 'Hilly' had firmly established himself as a Torquay United favourite and went into the game as United's joint top-scorer with Eifion Williams on nine goals.
The Gulls started the game brightly as Jason Rees opened the scoring with a 25-yard drive in the 10th minute, which helped to ease the nerves of the travelling Gulls' faithful.
On 25 minutes, United won a corner on the right hand side, which was taken by Paul Holmes and picked out 'Hilly' who nodded home his 10th goal of the season to give United a valuable two-goal cushion.
The hearts were in the mouths of the travelling Torquay supporters in the 40th minute when Barnet were awarded a penalty, after referee Richard Beeby adjudged Jimmy Aggrey to have handled the ball. The Bees' leading scorer Darren Currie stepped up to take the spot-kick, but Gulls keeper Stuart Jones guessed the direction of it correctly and saved it.
From the resulting goal kick United launched another attack, as Eifion Williams linked up with David Graham to extend the Gulls' lead to three goals before the half-time break.
In the second half, Barnet reduced their deficit to a single goal following a Ryan Green own goal and a Wayne Purser, which meant nerves were frayed in the final minutes of the game. However, United held on to clinch the win that secured their league status under the stewardship of Colin Lee.
3) Southend United 1 Torquay United 2, 8th May 2004
Three years later, the Gulls were venturing to the South East of England in very different circumstances to their trip to Barnet. United, now managed by Leroy Rosenior, knew their brief was simple: they had to better whatever result that Huddersfield Town achieved against Cheltenham Town at Whaddon Road to win automatic promotion for the first time in 38 years.
More than 2,500 Gulls' fans made the journey to Roots Hall and they saw their team get off to a flying start, as Steve Woods headed home an Alex Russell corner after three minutes.
Eight minutes later, United doubled their lead when David Graham nodded home a cross from Jo Kuffour as the Gulls put themselves firmly in the driving seat.
Southend hit back in the 17th minute through Lawrie Dudfield and the news coming through from Cheltenham wasn't good either as Huddersfield had taken the lead.
Kuffour came close to adding a third for United and Dudfield had another goal disallowed as the Gulls' destiny remained in the balance.
However, much to United's relief, Cheltenham managed to find an equaliser through Shane Duff and the Gulls also survived a late penalty decision after referee Tony Leake waved away appeals from the Shrimpers for a challenge by Reuben Hazell on Drewe Broughton.
But hang on they did, as the Gulls celebrated their first automatic promotion success since 1966.
4) Carlisle United 1 Torquay United 2, 29th April 2006
The Gulls' stay in League One proved to be a brief one, as they were relegated on the final day of the season following a 2-1 defeat against Colchester United.
On their return to League Two, they found themselves involved in another relegation battle to avoid dropping into the Conference and, after the appointment of Ian Atkins as manager, they launched another late bid for survival.
Wins over Macclesfield, Wrexham and Stockport County set them up nicely for an away clash with champions elect Carlisle United.
The Cumbrians started strongly, but the Gulls refused to cave in and took the lead on eight minutes when 'Hilly' connected with a cross from Jo Kuffour. It was his ninth goal of the campaign, and many observers likened his leap latch on to Kuffour's cross as the nearest thing they have seen to human flight!
Four minutes before the half-time interval, Kuffour found the target himself as his strike partner Lee Thorpe flicked a cross from Martin 'Buster' Phillips into his path and he fired home his fourth goal as many games with a shot on the turn.
Carlisle, who were looked to get their hands on the League Two title, weren't doing to go down without a fight and they pulled a goal back three minutes into the second half when Zigor Aranalde headed home a corner from Chris Lumsdon.
The pressure was now on the Gulls to defend and their central defensive pairing of Steve Woods and Craig Taylor against a Carlisle forward line, which included future United striker Karl Hawley and former Sunderland and Leeds striker Michael Bridges.
With ten minutes to go, Gulls' keeper Andy Marriott had appeared to have punched into his own net, but it was ruled out for an infringement and United held on to secure another vital win.
Carlisle were made to wait until the following Tuesday to get their hands on the league title, as they beat Mansfield Town, whilst a week later, Torquay made their safety a formality with a goalless draw with Boston United.
5) Torquay United 1 Exeter City 4, 5th May 2008
As a youngster, 'Hilly' was told by Exeter City that he was, as they described 'too small, not strong enough and couldn't win headers'. Given that he gained a reputation for being able to out jump opponents far taller than his own five feet nine inch frame, you wonder just how wrong you can be about someone!
It was then quite apt that he would equal Dennis Lewis's long-standing club appearance record against the Grecians.
The Gulls led City on aggregate after winning the first leg of their Conference Play-off semi-final 2-1 at St James Park.
'Hilly' was recalled to the starting line-up in place of Lee Phillips, and the decision by Paul Buckle to do so appeared to be paying dividends as he won a number of trademark headers in the first half.
When United did finally make the breakthrough, it was through 'Hilly' as he fired home in the 58th minute following good build-up play involving Tim Sills and Chris Zebroski.
For 'Hilly', it would be his final appearance for the Gulls at Plainmoor as he beat Lewis' record in the FA Trophy final against Ebbsfleet United before leaving United to sign for Dorchester Town.
Footnote: 'Hilly' is still playing for Exmouth Town, who he is joint player-manager of, in the South West Peninsula League and his love of playing still remains as strong as ever.