Roquebert's expedition to the Caribbean was an unsuccessful operation by a French naval squadron to transport supplies to Guadeloupe in December 1809 at the height of the Napoleonic Wars.

The squadron almost reached the Caribbean without encountering any of patrolling British warships sent to watch for French reinforcements, but was spotted and intercepted by the frigate HMS Junon on 13 December.

Destroying the badly damaged Junon and continuing with the mission, Roquebert successfully delivered the flûtes Loire and Seine to within sight of Guadeloupe and then left them, his frigates making their way back to France without ensuring the safe arrival of their convoy.

On 15 December, the small British brig HMS Observateur, which had witnessed the defeat of Junon, brought news of the French arrival to the blockade squadron anchored off Basse-Terre.

Summoning ships from the surrounding region, the British commander, Captain Volant Vashon Ballard amassed a significant squadron and forced the French flûtes to anchor in a protected bay at Anse à la Barque, on the southeastern coast of Guadeloupe.

With trade impossible, their economies stagnated while social upheaval and limited food supplies reduced their ability to resist invasion by the large British forces maintained in the region.

In the summer of 1808, desperate messages were sent to France from the islands, prompting a succession of French efforts to supply food, reinforcements and trading opportunities during the latter part of 1808 and the first months of 1809.

[3] The British blockade squadrons had intercepted a number of the messages sent from the islands during 1808, and a large expeditionary force was built up on Barbados with orders to invade and capture the French colonies as swiftly as possible.

Of the small ships despatched around the same time, none reached Guadeloupe; all were captured in the Western Atlantic or Caribbean by warships sent by Cochrane to patrol for approaching French reinforcements.

On 13 December, Shortland, in company with the 16-gun brig HMS Observateur under Captain Frederick Wetherall, stopped an American merchant ship and boarded her in search of contraband.

[13] As Observateur escaped, Junon was pounded from all sides, Roquebert's ship coming so close to the British frigate that their rigging tangled and they collided, inflicting further damage.

The French squadron was so close to Junon that the soldiers carried aboard for the garrison on Guadeloupe were able to fire their muskets at the British top deck, killing many of the sailors manning the guns.

[10] Within ten minutes of the first shot, Junon's top deck was almost completely cleared and Shortland had been taken below, his leg broken by grapeshot and his body pierced by several large wooden splinters.

The prisoners were dispersed among the French squadron and rather than spare the men required to repair and crew the battered Junon, Roquebert had the frigate set on fire and abandoned.

[15] On the same day that Observateur arrived off Basse-Terre, the frigate HMS Castor under Captain William Roberts had recaptured the merchant brig Ariel near La Désirade, taken by Roquebert's squadron two weeks earlier.

[15] In the aftermath of the destruction of Junon and the encounter with Castor, Roquebert decided to separate from the convoy and return to France, turning north with Clorinde and leaving the supply ships to make the journey to Guadeloupe independently.

[15] As Ballard's ships cruised along the coast in light winds, seeking a way into the well-protected anchorage, other batteries opened fire, one striking Ringdove off Pointe Lizard.

[16] The plan was initially frustrated by light winds, but by 14:25 Blonde and Thetis were within range of the gun batteries and fifteen minutes later they were able to open fire on the flûtes, although still at quite a distance.

[21] Roquebert's remaining frigates turned north after parting from the storeships, sighting the British squadron in the distance and grounding on a sandbar off Antigua in their haste to escape.

[17] They then returned to European waters, avoiding all contact with British shipping until 16 January 1810 at position 40°50′N 12°09′W / 40.833°N 12.150°W / 40.833; -12.150, approximately 200 nautical miles (370 km) west of the Portuguese coast, when they encountered the frigate HMS Virginie under Captain Edward Brace.

[22] Within a year, Roquebert and Saint-Cricq would be despatched on another mission to resupply a French colony, sailing with the frigate Néréide to Île de France in December 1810.

Unknown to the French authorities, a British expeditionary force had already captured the island, and Roquebert's squadron was ambushed in May 1811 and brought to battle off Tamatave in Madagascar.

In January 1810, the blockade tightened: Scorpion captured the brig Oreste from inside the harbour at Basse-Terre and Freija seized several coastal vessels in Baie-Mahault.

Over the rest of the month, the few remaining colonies belonging to France and the Netherlands were seized without opposition and the entire Caribbean was either under British or Spanish control, with the exception of the independent state of Haiti.