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In September 2017 Watkiss was appointed manager of Maltese Premier League side Naxxar Lions in Malta. He resigned for personal reasons from the position in November 2017.

On 26 October 2016 Watkiss returned to Grimsby on a temporary basis as joint caretaker manager with Dave Moore. Watkiss and Moore oversaw the club's 0-0 draw with Yeovil Town and 1-0 FA Cup defeat to Bolton Wanderers. In January 2017 Watkiss signed for the club on a permanent basis as a Development Coach.

On 4 November 2014 it was announced that Watkiss would become the first ever head coach of the Bharat FC for the 2014–15 season.

On 28 January 2013 Watkiss was appointed assistant manager of Stockport County on an initial three-month deal, working under Darije Kalezić.

On 11 September 2013 Watkiss rejoined Grimsby Town as the club's new youth team manager following the resignation of Adam Smith.

He was appointed as Development Coach by Phil Brown at Hull City in July 2009. Subsequent to the appointment of Steve Bruce as team manager, on 8 June 2012, Watkiss and fellow first team coach Steve Wigley left the club.

Grimsby appointed Mike Newell in October 2008 and Watkiss re-took his former position as Assistant Manager. At the end of the 2008–09 season, Watkiss was relieved of his duties at the club, and replaced by the club's Chief Scout, Brian Stein.

Following his dismissal he became Assistant Manager to Graham Rodger at Grimsby Town, and took over team affairs briefly in November 2006 following the sacking of Rodger, but he was overlooked for the job, which was given to Alan Buckley instead.

Watkiss continued in his role as Assistant Manager for the 2006–07 and 2007–08 campaigns, signing a new one-year contract in June 2007, he said "I'm absolutely delighted to be staying and I can't wait for the season to begin, I've learned so much from Alan in such a short time and I have really enjoyed working with him." He was once again given the role of Caretaker Manager

Watkiss became academy manager at Barnsley in September 2004, before his next port of call to manage Kidderminster Harriers an 18-month contract between 2004 and 2006.

As a player, he was a defender and notably played for Walsall, Hereford United and Mansfield Town. He became manager of Mansfield in 2002, and later Kidderminster Harriers. In 2006, he became assistant manager of Grimsby Town where he remained until 2009 where he then spent three years as a development coach at Hull City. He was briefly appointed assistant manager at Stockport County in 2013.

Following the resignation of Billy Dearden to take over at Notts County, Watkiss made the step up from assistant manager at Mansfield Town to become the team's manager in January 2002, where he guided them to their first promotion in 10 years. Due to his promotion success, he was then rewarded a three-year contract, butMansfield struggled in the 2002–03 season and by December 2002, following a 4–2 defeat away to Port Vale, the Stags were bottom of Division Two, Watkiss and assistant Neil Richardson were sacked after a meeting with Mansfield chairman Keith Haslam on the following Monday.

Watkiss remained at Mansfield Town as youth team coach taking over from Tony Ford, producing at least ten players who progressed into the first team during his three years in charge of the club's youth set-up. In June 2001, assistant manager Mark Kearney left to join Northampton Town as youth team coach. Speculation mounted that Watkiss would step up to assistant manager. Watkiss told the press "I do feel that the job would be a natural progression for me. A lot of the lads who have come up through the club were with me and I would like the chance to work with them again." A few of weeks later, the club's official website revealed that "the worst kept secret in the club's history had been confirmed", and Watkiss was promoted to assistant manager. Manager Billy Dearden explained, "I gave the position a lot of thought and have decided that Stuart is the best man for the job. He is a young coach who could go a long way in the game. He is at the right age to work with me, and it is a huge reward for him. He has done an excellent job with the youth team and it was a huge wrench to take him away from the youth team." Watkiss said "I am confident in my ability, I wouldn’t have gone for the job if not. Obviously time will tell if I am a success or not, but I am cautiously optimistic. It will be great working with Bill Dearden. He has a wealth of knowledge and experience within the game and I will be watching and learning all the time."

He went on to play for Rushall Olympic, Walsall, and Hereford United before moving to Mansfield Town in 1996, scoring his only goal for the Stags in a 2–4 win at Darlington in October when he met a Ben Sedgemore cross with a header which bounced downward and up into the top corner of the net. Watkiss remained with Town until hanging his boots up in 1999.

Watkiss started his playing career at Ward's Bridge School in his hometown of Wolverhampton. He then joined Willenhall Town, for the youth team, which reached the Midland Floodlit Youth League Cup final at Villa Park during the 1982–83 season. He later joined his home town club Wolverhampton Wanderers, where he served his apprenticeship as a 17-year-old. His debut was on 17 March 1984 in a Division One game with Sunderland; however, after making only two appearances, he joined West Midlands (Regional) League side Gresley Rovers in June 1985, before making a move to Crewe Alexandra in January 1986.

Stuart Watkiss (born 8 May 1966) is an English former professional footballer and manager.