Born in Forest Gate, Dennis Oli signed as a trainee for QPR in July 2005. He made roughly 30 appearances for Rangers, although most of them as substitute. In the 2003/04 season, Oli made 2 short-term loan moves to non-league sides Gravesend & Northfleet and then to Farnborough.|
After QPR's success campaign to gain promotion to the old Division One, Oli saw his chances limited and was released at the end of the 2003/04 season. After a successful trial spell, Swansea signed the young attacker on a month-to-month contract. However, in a season that saw Oli make only 1 substitute appearance for the Swans, his contract was not extended at the end of August 2004.
Dennis then joined Cambridge United where he spent little over a month featuring in just 4 games, scoring a single goal.
The pacey winger signed for Grays in November 2004. He played a key role in the club's Conference South and FA Trophy double, gaining a player of the month trophy for April along the way.
A lot of attention was drawn to Oli, in the following 2005/06 season, which was the Grays' first season at the top of the non-league pyramid. One of the clubs interested were local League One side, Southend United. However, Stimson, former Shrimper in his playing days, was reluctant to sell.
"A few clubs have been interested, Southend the most so, but I sat him down and told him that I think he will be bigger and better than Southend." Stimmo stated.
Oli went on the win the FA Trophy for the second year running with Grays Athletic, scoring the opening goal for The Blues against fellow Conference side Woking. Dennis also faced the harsh reality of being knocked out of the play-offs, before raising the Trophy.
The following 2006/07 season saw more interest shown in Dennis. This time Premiership new boys, Watford gave Oli a trial, however nothing came of this. It was also rumoured than Coventry boss, Iain Dowie had his eye on the quick-footed winger.
Despite all the interest and being linked with a move away, Dennis committed himself to a new two-year contract at the end of the 2006/07 season. In an interview with BBC Essex, Grays chairman Micky Woodard admired Dennis’ honesty in committing himself to Grays if he could not find a League club that suited him.
“He kept his word, unfortunately there was a couple of other people who promised to sign but went to other fields. Dennis was an honest man.” Woodward told BBC Essex’s Glen Speller.
Grays Ath announced on the 12th November 2007 that Dennis had signed for Gillingham on loan with a view to a permanent deal. A fee had been agreed as well as a 50% sell-on clause. Oli is ex-Blues manager Mark Stimson's first signing since taking the reigns at the Kent club. The deal was made permanent in January 2008.
Details correct as of 8th January 2008
Pictures © Grays Athletic 1982 Ltd.