2008–09
Drogba suffered a string of injuries early on in the season and struggled to regain fitness, missing games from August to November due to knee problems. He scored his first goal of the season in mid-November but there was little reason to celebrate: he incurred disciplinary action and a three match ban for throwing a coin back into the stands and Chelsea suffered a League Cup defeat against Burnley. Drogba scored his second goal of the season in a 2–1 victory against CFR Cluj in the UEFA Champions League, while his first Premier League goal of the season came in a 2–0 win against West Bromwich Albion in late December 2008. Having missed many games through injury and suspension, Drogba had lost his first team place and manager Scolari favoured playing Nicolas Anelka as a lone striker rather than pairing the two. However, he resolved to regain his position in the squad and Chelsea remained keen to keep the Ivorian.Upon the temporary appointment of Guus Hiddink in early February following the sacking of Scolari, Drogba enjoyed a rejuvenation of sorts, returning to his rich goal-scoring form with four goals in five games after the new manager took over. His revival in form saw him net twice against Bolton Wanderers, and four times in four Champions League matches, one in each leg of the last sixteen and quarter final of the competition against Juventus and Liverpool respectively, with these goals ensuring Chelsea's passage into the semi-finals. Just four days after his Champions League heroics, Drogba scored a late winner in the FA Cup semi-final match against Arsenal after Frank Lampard's superb pass found Drogba and he carefully rounded Arsenal goalkeeper Łukasz Fabiański before slotting into an empty net. Drogba also caused controversy after Chelsea's Champions League semi-final defeat at the hands of Barcelona. Feeling that many decisions had gone against Chelsea, substituted Drogba confronted referee Tom Henning Øvrebø after the final whistle. He received a yellow card in the process and was recorded shouting "It's a fucking disgrace" into a live television camera. On 17 June 2009, UEFA subsequently handed him a six game European ban with the final two games suspended.The ban then was cut down by 1 match after an appeal by Chelsea. In the 2009 FA Cup Final he scored Chelsea's first and equalising goal as they went on to win 2–1. This was his sixth goal in a major cup final in England. Although Drogba had previously expressed his desire to switch clubs, he decided to remain with the Blues under new coach Carlo Ancelotti and sign a new contract.
2009–10
Drogba began the season in fine form for Chelsea, netting a penalty during a shoot-out in the Community Shield over Manchester United, before scoring twice in a 2–1 victory over Hull City. Drogba earned himself an assist when he was fouled in the area to give Chelsea a penalty, which Frank Lampard duly converted, in a 3–1 victory over Sunderland. In Chelsea's third game of the season against West-London rivals Fulham, Drogba scored his third goal of the season. Drogba scored his fourth goal of the season, against Stoke City; Chelsea ended winning the game 2–1 with a late strike from Malouda. He added a fifth at home against London rivals Tottenham Hotspur on 20 September. He scored his 100th goal for Chelsea in a 3–1 defeat against Wigan Athletic. Drogba was again important in the 2–0 win over title rivals Liverpool on 4 October. He assisted both goals, setting up Nicolas Anelka and Florent Malouda. He then scored a glancing header against Blackburn on 24 October 2009, bringing his tally to an impressive eight goals in eleven appearances, scoring his third goal in as many games. Drogba continued his fine form scoring a header against Bolton Wanderers in a 4–0 thrashing in the Carling Cup, Drogba went on to score a fine team goal in the same week with another 4–0 win against Bolton Wanderers in the Premier League.After missing the first three Champions League matches for Chelsea with a ban, Drogba started the fourth game against Spanish side Atlético Madrid. He scored two goals in the last ten minutes and the match ended 2–2. The latter being a fine solo effort in which he beat a number of the opposition players and had his first effort saved by the goalkeeper but then slotted in the rebound. On 29 November, Drogba scored a brace against London rivals Arsenal at the Emirates Stadium, the second of which a free kick from outside the box. It brought his tally for the season to 14 goals in 16 games. On 12 December, Drogba continued to impress with 2 goals in 3–3 draw against Everton.
Between 3 and 30 January Drogba was on Africa Cup of Nations duty and came back on 2 February against Hull City where he scored a 40th minute equaliser to tie the game 1–1. On 24 March, Drogba scored his 30th goal of the season in an away game against Portsmouth.
On 9 May, Drogba inspired Chelsea to win the Premier League by scoring a hat-trick in an 8–0 win over Wigan Athletic. In doing so, he not only collected his third League winner's medal, but also won the Golden Boot for the season, his second time doing so, by topping the chart with 29 league goals, beating Wayne Rooney to the title who remained on 26 goals. Both players had the same number of goals (26) before the start of their respective fixtures. However, during the game, Drogba appeared to be clearly angry with team-mate and regular penalty taker Frank Lampard, after Lampard refused to let Drogba take a penalty which would lead Chelsea to go 2–0 up and give him a chance of winning the golden boot. Lampard scored the penalty, but Drogba did not celebrate with his team-mates. Later on in the game though Ashley Cole was tripped in the box when Chelsea were already 5–0 up, and this time Lampard allowed Drogba to take the penalty, which he scored to go two goals clear of Rooney.