three days later, on 12 August 2008, in the club's 2–2 draw with Rotherham United in the League Cup. Smith made infrequent appearances in his first three months with Wednesday, starting just four games up during his loan spell, as well as making a further nine appearances from the substitute's bench. This was not helped by the first red card of his career in a 3–1 away defeat to Birmingham City, receiving a four-match ban "for leading with his elbow in a challenge on Stuart Parnaby". After serving the suspension, Smith was unable to hold down a place in the Sheffield Wednesday first-team, returning to Chelsea upon the expiry of his loan deal in early January 2009. Leyton Orient Smith was loaned out once again in February 2009, this time joining League One side Leyton Orient for the remainder of the 2008–09 season. He was brought in by then-caretaker manager Kevin Nugent, who said – "Jimmy is joining from Chelsea and he will be a good addition to the squad. He has great ability and can play anywhere across the midfield". Smith made his debut for the club five days after joining, on 7 February, playing the whole match in the club's 0–0 away draw at Tranmere Rovers. He played regularly throughout the rest of the season, scoring his first goal for the club in a 2–1 victory over Colchester United at Brisbane Road in April 2009, a late winner that ensured Orient had all but secured their League One status for another season. Smith made 16 appearances during the successful loan spell, scoring once, as the club went from inside the relegation zone to finishing comfortably in mid-table during his three-month stay. He returned to Chelsea at the end of the season with a year remaining on his contract, but opted to leave the club to sign for Leyton Orient on a permanent basis, signing a two-year deal with the East London club. On the move, Smith stated – "The best thing about Orient is I know where I'm going to be from one week to the next. It's the reason I left Chelsea even though I had a year left on my contract". The 2009–10 campaign began with Smith scoring the winning goal on the opening day of the season, lifting the ball over Fraser Forster with just twenty minutes remaining to earn Orient a 2–1 victory away